JPWO2018100907A1 - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
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- JPWO2018100907A1 JPWO2018100907A1 JP2018553703A JP2018553703A JPWO2018100907A1 JP WO2018100907 A1 JPWO2018100907 A1 JP WO2018100907A1 JP 2018553703 A JP2018553703 A JP 2018553703A JP 2018553703 A JP2018553703 A JP 2018553703A JP WO2018100907 A1 JPWO2018100907 A1 JP WO2018100907A1
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- light emitting
- emitting layer
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Abstract
高効率、長寿命、かつ屈曲耐性のある有機エレクトロルミネッセンス素子を提供する。陽極(12)と陰極(18)との間に、発光層(15)と、発光層(15)に隣接する電子輸送層(16)とを備える有機エレクトロルミネッセンス素子(10)であって、発光層(15)のホスト化合物のイオン化ポテンシャルが発光層(15)の発光ドーパントのイオン化ポテンシャルより0.3eV以上深く、電子輸送層(16)に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上である。Provided is an organic electroluminescence device having high efficiency, long life, and bending resistance. An organic electroluminescence device (10) comprising a light emitting layer (15) and an electron transport layer (16) adjacent to the light emitting layer (15) between an anode (12) and a cathode (18), wherein The ionization potential of the host compound of the layer (15) is 0.3 eV or more deeper than the ionization potential of the light emitting dopant of the light emitting layer (15), and the molecular dipole moment of at least one organic compound contained in the electron transport layer (16) is 6 0.0 Debye or more.
Description
本発明は、有機エレクトロルミネッセンス素子に関する。 The present invention relates to an organic electroluminescence element.
有機エレクトロルミネッセンス素子(以下、適宜、有機EL素子という)の面発光及び高効率光源としての魅力が高まるにつれ、高効率、長寿命、低コストの全てを満足させる有機EL素子が必要とされている。
更に、光源における、薄い、軽い、曲がるといった魅力を最大限に発揮するため、フレキシブルパネル上に有機EL素子を形成したフレキシブルディスプレイやフレキシブル照明の開発が進められている。そして、これらフレキシブルディスプレイやフレキシブル照明を実現するために、高い製造技術及び素材技術が必要とされている。特に、屈曲に対し、輝度低下、ダークスポットの発生、輝度ムラの無いフレキシブルパネルが求められている。As the surface emission of organic electroluminescence elements (hereinafter referred to as organic EL elements as appropriate) and the attractiveness as high-efficiency light sources increase, organic EL elements that satisfy all of high efficiency, long life, and low cost are required. .
Furthermore, in order to maximize the attractiveness of the light source, such as being thin, light, and curved, development of flexible displays and flexible illuminations in which organic EL elements are formed on a flexible panel is in progress. And in order to implement | achieve these flexible displays and flexible illumination, a high manufacturing technique and material technology are required. In particular, there is a demand for a flexible panel that is free from luminance reduction, dark spot generation, and luminance unevenness with respect to bending.
これらの要求に対しては、各機能材料を用い、蒸着法により多積層構造を形成する方法により高性能化が進んでいる。しかしながら、高い真空度を実現するための製造設備や材料利用効率の低さから、製造コストが高くなる問題がある。一方、製造コストを下げる方法として、湿式法(塗布法ともいう)により各機能材料を積層する方法がある。 In response to these requirements, higher performance has been promoted by a method of forming each of the functional materials and forming a multi-layer structure by vapor deposition. However, there is a problem that the manufacturing cost increases due to the low manufacturing equipment and material utilization efficiency for realizing a high degree of vacuum. On the other hand, as a method of reducing the manufacturing cost, there is a method of laminating each functional material by a wet method (also called a coating method).
しかしながら、層を構成する機能材料の多くは、化学的に似たような構造骨格からなる物質が多く、このことは塗布により積層するための溶媒への溶解性が近く、積層時に混合してしまうことを意味する。溶媒と溶質の溶解度差により積層を試みた場合でも、3〜4層の積層が限界である。そのため、湿式法の場合、蒸着法のような機能分離多積層構造をとることが難しく、湿式法により各機能材料を積層する方法において、低電圧による高効率化と長寿命化とを両立するためには、技術的に非常に高いハードルがあった。 However, many of the functional materials that make up a layer are mostly substances that have a structural skeleton that is chemically similar, and this is close to solubility in a solvent for laminating by coating, and mixes during laminating. Means that. Even when stacking is attempted due to the difference in solubility between the solvent and the solute, stacking of 3 to 4 layers is the limit. Therefore, in the case of the wet method, it is difficult to adopt a function-separated multi-layer structure as in the vapor deposition method, and in the method of laminating each functional material by the wet method, to achieve both high efficiency by low voltage and long life. Had technically very high hurdles.
また、高効率化と長寿命化との両立を図るため、電子輸送材に極性化合物を使用する技術が開示されている(例えば、特許文献1〜4参照)。
特許文献1には、極性正孔阻止材料としてヘテロ窒素を含む多員環化合物が開示されている。しかしながら、これらの化合物は、成膜に溶剤を使用した場合の膜密度や膜内の電子輸送性を考慮したものではなく、これらの化合物を用いた有機EL素子は、性能において改善の余地がある。Moreover, in order to achieve both high efficiency and long life, a technique using a polar compound as an electron transport material has been disclosed (for example, see Patent Documents 1 to 4).
Patent Document 1 discloses a multi-membered ring compound containing heteronitrogen as a polar hole blocking material. However, these compounds do not take into consideration the film density and the electron transport property in the film when a solvent is used for film formation, and there is room for improvement in the performance of organic EL devices using these compounds. .
また、特許文献2では、フォスフィンオキシド系電子輸送材とアルカリ金属錯体を共蒸着することで高極性を実現している。しかしながら、アルカリ金属錯体がクエンチャーを生成するため、有機発光素子の性能が低下する問題がある。また、塗布により成膜する場合には、錯体の解離が十分ではなく、フォスフィンオキシド系電子輸送材とアルカリ金属錯体を用いる効果が得られない。 Moreover, in patent document 2, high polarity is implement | achieved by co-evaporating a phosphine oxide type electron transport material and an alkali metal complex. However, since the alkali metal complex generates a quencher, there is a problem in that the performance of the organic light emitting device is deteriorated. Moreover, when forming into a film by application | coating, dissociation of a complex is not enough and the effect using a phosphine oxide type electron transport material and an alkali metal complex is not acquired.
また、特許文献3では、電子輸送層を構成する材料に、2デバイ以上の双極子モーメントを有する材料を混合している。しかしながら、2デバイ以上の双極子モーメントを有する材料として発光性のドーパントと同じ化合物を使用しており、少なからず電子輸送材との界面発光が存在する。そのため、有機EL素子において高性能を得るためには十分とは言えない。また、発光層の成分と同じ成分を塗布して電子輸送層を成膜する場合、可溶溶媒により下層が洗い流されるため、塗布型の有機EL素子では十分な効果が得られない問題がある。 Moreover, in patent document 3, the material which has a dipole moment of 2 debyes or more is mixed with the material which comprises an electron carrying layer. However, the same compound as the luminescent dopant is used as a material having a dipole moment of 2 Debye or more, and there is a considerable amount of interfacial light emission with an electron transport material. Therefore, it cannot be said that it is sufficient for obtaining high performance in the organic EL element. In addition, when the same component as the component of the light emitting layer is applied to form an electron transport layer, the lower layer is washed away with a soluble solvent, and thus there is a problem that a sufficient effect cannot be obtained with a coating type organic EL element.
また、特許文献4では、ホスト材料として極性の高い電子輸送材を使用し、低電圧化を図っている。しかしながら、極性が強すぎると再結合確率の低下及び発光材料との相互作用による発光効率の低下を引き起こすため、有機EL素子の性能は十分とは言えない。また、電子移動が速くなりすぎること、発光材と電子輸送材とが共存してしまうことが問題となる。 In Patent Document 4, an electron transport material having a high polarity is used as the host material to reduce the voltage. However, if the polarity is too strong, the recombination probability is lowered and the light emission efficiency is lowered due to the interaction with the light emitting material. Therefore, the performance of the organic EL element is not sufficient. Moreover, it becomes a problem that an electron transfer becomes too quick, and a luminescent material and an electron transport material coexist.
更に、いずれの特許文献においても、フレキシブル基板上に素子を作製した場合の屈曲耐久性については触れておらず、これらの極性化合物を用いた有機EL素子は、屈曲耐久性において改善の余地がある。 Furthermore, none of the patent documents mentions bending durability when an element is produced on a flexible substrate, and organic EL elements using these polar compounds have room for improvement in bending durability. .
本発明は、高効率、長寿命、かつ屈曲耐性のある有機エレクトロルミネッセンス素子を提供することを課題とする。 An object of the present invention is to provide an organic electroluminescence device having high efficiency, long life, and bending resistance.
本発明者は、上記課題を解決すべく、上記問題の原因等について検討する過程において、以下の事項を見出した。
高効率、長寿命の青色りん光発光が得られる材料は、高S1化及び高T1化の観点から、また、不純物や未反応基によるクエンチの観点から、低分子の物質である。これらの高性能化のために、発光層の隣接層には、発光層からの電荷ブロック及び励起子ブロックの機能が必要となる。更に、発光層及び電子輸送層に双極子モーメントの大きい材料を使用することで発生する界面電界により、注入障壁を緩和し低電圧化を図ることができる。In order to solve the above problems, the present inventor has found the following matters in the process of examining the cause of the above problems and the like.
A material capable of obtaining blue phosphorescence having high efficiency and long life is a low molecular substance from the viewpoint of increasing S1 and T1 and from the viewpoint of quenching by impurities and unreacted groups. In order to achieve these high performances, the function of the charge block and exciton block from the light emitting layer is required in the adjacent layer of the light emitting layer. Furthermore, the injection barrier can be relaxed and the voltage can be lowered by the interface electric field generated by using a material having a large dipole moment for the light emitting layer and the electron transporting layer.
本発明では、双極子モーメントが6.0デバイ以上の電子輸送材により低電圧化及び長寿命化を達成することができる。
ただし、低分子の発光材料が、ヘテロ原子が多く含まれる塩基性(求核性)の大きい電子輸送材に直接触れると、配位子交換や錯形成等により発光のクエンチャーが生成し、発光効率が低下する問題がある。In the present invention, a low voltage and a long life can be achieved by an electron transport material having a dipole moment of 6.0 debye or more.
However, when a low-molecular light-emitting material directly touches a basic (nucleophilic) electron transport material that contains many heteroatoms, a light-emitting quencher is generated due to ligand exchange or complex formation, resulting in light emission. There is a problem that efficiency decreases.
本発明では、発光層に発光材料よりも深いイオン化ポテンシャル(以下、適宜、Ipという)(Δ0.3eV以上)のホスト化合物を使用することで、高効率、長寿命の両立が可能であることを見出した。これは、ドーパントのIpがホールトラップとなり正孔輸送層側で再結合するため、電子輸送材の影響を受けにくいためと考えられる。 In the present invention, by using a host compound having an ionization potential deeper than that of the light emitting material (hereinafter referred to as Ip) (Δ0.3 eV or more) for the light emitting layer, both high efficiency and long life can be achieved. I found it. This is presumably because the dopant Ip becomes a hole trap and recombines on the hole transport layer side, so that it is not easily affected by the electron transport material.
更に、電子輸送材分子のπ共役内において、N(窒素)間の距離が短いこと及びダイポールが大きいことで分子内輸送性が向上する。また、N密度が高いことで各種溶媒への溶解性が高くアモルファス性を維持できる一方で、隣接分子間相互作用が多く、膜形成時に高密度化し、性能低下要因である溶媒を追い出し易いだけでなく、基板に並行に分子配向するため外部取り出し効率が向上する。また、N密度が高いことで高密度化した膜は、素子駆動で発生する熱による膜質変化に強い。更に、N密度が高いことで高密度化した膜は、素子内に侵入してくる酸素・水等の発光層への到達を抑制するため、高温保存時の輝度低下が抑制され、曲げにより有機層にクラックが入った場合の高電圧化も抑制できることが分かった。 Further, the intramolecular transportability is improved by the short distance between N (nitrogen) and the large dipole in the π conjugate of the electron transport material molecule. In addition, the high N density makes it highly soluble in various solvents and maintains an amorphous state, while there are many interactions between adjacent molecules, increasing the density during film formation, and easily driving off the solvent that is the cause of performance degradation. In addition, since the molecules are aligned in parallel with the substrate, the external extraction efficiency is improved. In addition, a film having a high density due to a high N density is resistant to film quality changes due to heat generated by element driving. Furthermore, the film densified by the high N density suppresses the arrival of oxygen, water, etc. entering the device into the light emitting layer, so that the decrease in luminance during high-temperature storage is suppressed, and the organic matter is bent. It was found that high voltage can be suppressed when cracks occur in the layer.
本発明の効果は、発光層及び電子輸送層が共に塗布により成膜される場合に発揮されやすい。塗布により成膜される場合のほうが、蒸着により成膜する場合よりも界面混合が顕著であり、発光材料が電子輸送材料の影響をより受けやすいが、このような場合でも、高効率化、長寿命化、屈曲耐久性の効果を発揮することができ、また、ブロック層などを挿入する必要がなくなるため、製造コストを下げることができる。本発明は、特に、積層数が増やせない塗布による成膜により製造される場合に適したものである。 The effect of the present invention is easily exhibited when both the light emitting layer and the electron transport layer are formed by coating. Interfacial mixing is more pronounced when the film is formed by coating than when it is formed by vapor deposition, and the light emitting material is more susceptible to the effects of electron transport materials. The effects of life extension and bending durability can be exhibited, and it is not necessary to insert a block layer or the like, so that the manufacturing cost can be reduced. The present invention is particularly suitable in the case of being manufactured by film formation by coating that cannot increase the number of stacked layers.
本発明の上記課題は、以下の手段により解決される。 The above-described problems of the present invention are solved by the following means.
1.陽極と陰極との間に、発光層と、前記発光層に隣接する電子輸送層とを備える有機エレクトロルミネッセンス素子であって、前記発光層のホスト化合物のイオン化ポテンシャルが前記発光層の発光ドーパントのイオン化ポテンシャルより0.3eV以上深く、前記電子輸送層に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上である有機エレクトロルミネッセンス素子。 1. An organic electroluminescence device comprising a light emitting layer and an electron transport layer adjacent to the light emitting layer between an anode and a cathode, wherein the ionization potential of a host compound of the light emitting layer is an ionization of a light emitting dopant of the light emitting layer An organic electroluminescence device, wherein a molecular dipole moment of at least one organic compound included in the electron transport layer is 6.0 debyes or more deeper than a potential by 0.3 eV or more.
2.前記有機化合物の分子双極子モーメントが8.0デバイ以上である前記1に記載の有機エレクトロルミネッセンス素子。 2. 2. The organic electroluminescence device according to 1, wherein the organic compound has a molecular dipole moment of 8.0 debye or more.
3.前記有機化合物の分子双極子モーメントが10.0デバイ以上である前記1に記載の有機エレクトロルミネッセンス素子。 3. 2. The organic electroluminescence device according to 1, wherein the organic compound has a molecular dipole moment of 10.0 Debye or more.
4.前記有機化合物の分子双極子モーメントが12.0デバイ以上である前記1に記載の有機エレクトロルミネッセンス素子。 4). 2. The organic electroluminescence device according to 1, wherein the organic compound has a molecular dipole moment of 12.0 debye or more.
5.前記有機化合物が下記一般式(1)で表される化合物である前記1から前記4のいずれか一項に記載の有機エレクトロルミネッセンス素子。 5. 5. The organic electroluminescence device according to any one of 1 to 4, wherein the organic compound is a compound represented by the following general formula (1).
[式中Z1とZ2は、各々独立に、置換基を有していてもよい、6員の芳香族炭化水素環又は6員の芳香族複素環を表し、Z3は単なる結合手を表す。R101は置換基を有していてもよいアリール基又は置換基を有していてもよい芳香族複素環基を表す。][In the formula, Z 1 and Z 2 each independently represent a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring which may have a substituent, and Z 3 represents a simple bond. To express. R 101 represents an aryl group which may have a substituent or an aromatic heterocyclic group which may have a substituent. ]
6.前記一般式(1)中、Z1が置換基を有していてもよいピリジン環を表し、Z2が置換基を有していてもよいベンゼン環を表す前記5に記載の有機エレクトロルミネッセンス素子。6). In the general formula (1), Z 1 represents a pyridine ring optionally having a substituent, an organic electroluminescent device according to the 5 Z 2 represents a benzene ring which may have a substituent .
7.前記一般式(1)中、Z1及びZ2が置換基を有していてもよいピリジン環を表す前記5に記載の有機エレクトロルミネッセンス素子。7). 6. The organic electroluminescence device according to 5, wherein Z 1 and Z 2 in the general formula (1) represent a pyridine ring which may have a substituent.
8.前記有機化合物が炭素と窒素と水素のみから成る、一般式(1)で表される化合物である前記5から前記7のいずれか一項に記載の有機エレクトロルミネッセンス素子。 8). 8. The organic electroluminescence device according to any one of 5 to 7, which is a compound represented by the general formula (1), wherein the organic compound is composed of only carbon, nitrogen, and hydrogen.
9.前記有機エレクトロルミネッセンス素子の各構成層全体として、極性フッ化溶媒が1000質量ppm以下含有されている前記1から前記8のいずれか一項に記載の有機エレクトロルミネッセンス素子。 9. 9. The organic electroluminescence device according to any one of 1 to 8, wherein a polar fluorinated solvent is contained in an amount of 1000 ppm by mass or less as a whole of each constituent layer of the organic electroluminescence device.
10.前記極性フッ化溶媒が、フッ化アルコール、フッ化エステル及びフッ化エーテルから選ばれるいずれか1つ以上の溶媒である前記9に記載の有機エレクトロルミネッセンス素子。 10. 10. The organic electroluminescence device according to 9, wherein the polar fluorinated solvent is any one or more solvents selected from fluorinated alcohol, fluorinated ester and fluorinated ether.
11.前記極性フッ化溶媒が、炭素原子数3〜5のフッ化アルコールを含有する前記9又は前記10に記載の有機エレクトロルミネッセンス素子。 11. 11. The organic electroluminescence device according to 9 or 10, wherein the polar fluorinated solvent contains a fluorinated alcohol having 3 to 5 carbon atoms.
12.前記発光層が、分子量3000以下の化合物で構成されている前記1から前記11のいずれか一項に記載の有機エレクトロルミネッセンス素子。 12 12. The organic electroluminescence device according to any one of 1 to 11, wherein the light emitting layer is composed of a compound having a molecular weight of 3000 or less.
13.前記発光層の膜厚が50nm以上である前記1から前記12のいずれか一項に記載の有機エレクトロルミネッセンス素子。 13. 13. The organic electroluminescence device according to any one of 1 to 12, wherein the light emitting layer has a thickness of 50 nm or more.
本発明によれば、高効率、長寿命、かつ屈曲耐性のある有機エレクトロルミネッセンス素子を提供することができる。 According to the present invention, it is possible to provide an organic electroluminescence element having high efficiency, long life, and bending resistance.
以下、本発明を実施するための形態について詳細に説明するが、本発明はこれらに限定されるものではない。なお、本願において、「〜」は、その前後に記載される数値を下限値及び上限値として含む意味で使用する。 Hereinafter, although the form for implementing this invention is demonstrated in detail, this invention is not limited to these. In addition, in this application, "-" is used in the meaning which includes the numerical value described before and behind that as a lower limit and an upper limit.
《有機エレクトロルミネッセンス素子》
有機EL素子は、陽極と陰極との間に、発光層と、発光層に隣接する電子輸送層とを備える。
そして、有機EL素子は、発光層のホスト化合物のイオン化ポテンシャルが発光層の発光ドーパントのイオン化ポテンシャル(Ip)より0.3eV以上深い。
更に、有機EL素子は、電子輸送層に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上である。《Organic electroluminescence device》
The organic EL element includes a light emitting layer and an electron transport layer adjacent to the light emitting layer between an anode and a cathode.
In the organic EL element, the ionization potential of the host compound in the light emitting layer is 0.3 eV or more deeper than the ionization potential (Ip) of the light emitting dopant in the light emitting layer.
Furthermore, in the organic EL element, the molecular dipole moment of at least one organic compound contained in the electron transport layer is 6.0 debye or more.
イオン化ポテンシャルは化合物のHOMO(最高被占分子軌道)レベルにある電子を真空準位に放出するのに必要なエネルギーとして、また、双極子モーメントは化合物の密度汎関数計算から求められる電子密度の偏りの負電荷から正電荷へのベクトルとその大きさの積で定義され、例えば下記に示すような方法により求めることができる。 The ionization potential is the energy required to discharge electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and the dipole moment is the deviation of the electron density obtained from the density functional calculation of the compound. Is defined by the product of the vector from the negative charge to the positive charge and its magnitude, and can be determined by the following method, for example.
(1)イオン化ポテンシャル及び双極子モーメントは、米国Gaussian社製の分子軌道計算用ソフトウェアであるGaussian98(Gaussian98、Revision A.11.4,M.J.Frisch,et al,Gaussian,Inc.,Pittsburgh PA,2002.)を用い、キーワードとしてB3LYP/6−31G*を用いて構造最適化を行うことによりそれぞれ算出した値(イオン化ポテンシャルの場合はeV単位換算値、双極子モーメントの場合はデバイ単位換算値)の小数点第2位、あるいは第3位を四捨五入した値として求めることができる。この計算値が有効な背景には、この手法で求めた計算値と実験値の相関が高いためである。 (1) The ionization potential and the dipole moment are measured according to Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, software for molecular orbital calculation manufactured by Gaussian, USA. , 2002.) and values calculated by performing structural optimization using B3LYP / 6-31G * as a keyword (eV unit converted value for ionization potential, Debye unit converted value for dipole moment) ) In the second decimal place or the third decimal place. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
(2)イオン化ポテンシャルは光電子分光法で直接測定する方法により求めることもできる。例えば、理研計器社製の低エネルギー電子分光装置「Model AC−2」を用いて、あるいは紫外光電子分光として知られている方法を好適に用いることができる。 (2) The ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a method known as ultraviolet photoelectron spectroscopy can be suitably used by using a low energy electron spectrometer “Model AC-2” manufactured by Riken Keiki Co., Ltd.
《有機EL素子の構成》
本発明の有機EL素子の構成について、図1を参照して説明する。図1は、有機EL素子の一例である有機EL素子10の概略断面図である。<< Configuration of organic EL element >>
The configuration of the organic EL element of the present invention will be described with reference to FIG. FIG. 1 is a schematic cross-sectional view of an
有機EL素子10は、基材11、陽極12、正孔注入層13、正孔輸送層14、発光層15、電子輸送層16、電子注入層17及び陰極18をこの順に備えている。
The
有機EL素子の素子構成としては、図1に示す構成例に限られるものではなく、例えば、代表的な素子構成の層構成として以下の構成を挙げることができる。
(1)発光層/電子輸送層
(2)正孔輸送層/発光層/電子輸送層
(3)正孔輸送層/発光層/電子輸送層/電子注入層
(4)正孔注入層/正孔輸送層/発光層//電子輸送層
(5)正孔注入層/正孔輸送層/発光層//電子輸送層/電子注入層
(6)正孔注入層/正孔輸送層/電子阻止層/発光層/電子輸送層/電子注入層
上記の中で(5)及び(6)の構成が好ましく用いられるが、これに限定されるものではない。The element configuration of the organic EL element is not limited to the configuration example illustrated in FIG. 1. For example, the following configurations can be given as a typical layer configuration of the element configuration.
(1) Light emitting layer / electron transport layer (2) Hole transport layer / light emitting layer / electron transport layer (3) Hole transport layer / light emitting layer / electron transport layer / electron injection layer (4) Hole injection layer / positive Hole transport layer / light emitting layer // electron transport layer (5) Hole injection layer / hole transport layer / light emitting layer // electron transport layer / electron injection layer (6) Hole injection layer / hole transport layer / electron blocking Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer Among the above, the configurations of (5) and (6) are preferably used, but are not limited thereto.
発光層は、単層又は複数層で構成される。また、必要に応じて、発光層と陰極との間に正孔阻止層(正孔障壁層)や電子注入層(陰極バッファー層)等が設けられてもよく、発光層と陽極との間に電子阻止層(電子障壁層)や正孔注入層(陽極バッファー層)等が設けられてもよい。これらの各層は、本発明の規定を満たす限り、公知の材料及び方法で形成することができる。 The light emitting layer is composed of a single layer or a plurality of layers. If necessary, a hole blocking layer (hole blocking layer), an electron injection layer (cathode buffer layer) or the like may be provided between the light emitting layer and the cathode, and between the light emitting layer and the anode. An electron blocking layer (electron barrier layer), a hole injection layer (anode buffer layer), or the like may be provided. Each of these layers can be formed by known materials and methods as long as the definition of the present invention is satisfied.
《発光層》
発光層は、電極又は隣接層から注入される電子と正孔とが再結合し、励起子を経由して発光する場を提供する層である。発光層は、発光ドーパント(発光性ドーパント化合物、ドーパント化合物、単にドーパントともいう。)と、ホスト化合物(マトリックス材料、発光ホスト化合物、単にホストともいう。)とを含有する。<Light emitting layer>
The light emitting layer is a layer that provides a field in which electrons and holes injected from an electrode or an adjacent layer are recombined to emit light via excitons. The light emitting layer contains a light emitting dopant (a light emitting dopant compound, a dopant compound, also simply referred to as a dopant) and a host compound (a matrix material, a light emitting host compound, also simply referred to as a host).
また、発光層を構成する発光層材料は、分子量3000以下の化合物であるものとしてもよい。分子量3000以下の化合物とすることで、溶媒に対する溶解性が向上する。なお、好ましくは、分子量500以上である。 The light emitting layer material constituting the light emitting layer may be a compound having a molecular weight of 3000 or less. By using a compound having a molecular weight of 3000 or less, solubility in a solvent is improved. Preferably, the molecular weight is 500 or more.
また、発光層材料として使用される発光ドーパント及びホスト化合物の分子量は特に限定されるものではないが、本発明に係る発光層は、ジベンゾフラン環、ジベンゾチオフェン環又はカルバゾール環を有し、かつアルキル基、アルケニル基、アルキニル基又はアリールアルキル基を有しない化合物を含有することが好ましい。 The molecular weight of the light emitting dopant and the host compound used as the light emitting layer material is not particularly limited, but the light emitting layer according to the present invention has a dibenzofuran ring, a dibenzothiophene ring or a carbazole ring, and an alkyl group. It is preferable to contain a compound having no alkenyl group, alkynyl group or arylalkyl group.
発光層の膜厚は特に限定されるものではないが、再結合領域と電子輸送層との距離の観点から、50nm以上であることが好ましく、70nm以上であることがより好ましい。また、駆動電圧の観点から、150nm以下であることが好ましい。 The thickness of the light emitting layer is not particularly limited, but is preferably 50 nm or more, and more preferably 70 nm or more from the viewpoint of the distance between the recombination region and the electron transport layer. Moreover, it is preferable that it is 150 nm or less from a viewpoint of a drive voltage.
発光層の形成方法は特に制限はなく、例えば、従来公知の真空蒸着法や湿式法等により形成することができる。中でも、有機EL素子の製造コストを低減する観点から、湿式法で形成することが好ましい。 There is no restriction | limiting in particular in the formation method of a light emitting layer, For example, it can form by a conventionally well-known vacuum evaporation method, a wet method, etc. Especially, it is preferable to form by a wet method from a viewpoint of reducing the manufacturing cost of an organic EL element.
湿式法としては、例えば、スピンコート法、キャスト法、インクジェット法、印刷法、ダイコート法、ブレードコート法、ロールコート法、スプレーコート法、カーテンコート法、LB法(ラングミュア−ブロジェット法)等を用いることができる。中でも、均質な薄膜が得られやすく、かつ高生産性の点から、ダイコート法、ロールコート法、インクジェット法、スプレーコート法等のロールtoロール方式に適用可能な方法が好ましい。 Examples of the wet method include spin coating, casting, ink jet, printing, die coating, blade coating, roll coating, spray coating, curtain coating, LB (Langmuir-Blodgett), and the like. Can be used. Among them, a method applicable to a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, or a spray coating method is preferable from the viewpoint of obtaining a homogeneous thin film easily and high productivity.
湿式法において、発光層材料を溶解又は分散する液媒体としては、例えば、メチルエチルケトン、シクロヘキサノン等のケトン類、酢酸エチル等の脂肪酸エステル類、ジクロロベンゼン等のハロゲン化炭化水素類、トルエン、キシレン、メシチレン、シクロヘキシルベンゼン等の芳香族炭化水素類、シクロヘキサン、デカリン、ドデカン等の脂肪族炭化水素類、ジメチルホルムアミド(DMF)、ジメチルスルホキシド(DMSO)等の有機溶媒を用いることができる。
また、発光層材料を液媒体中に分散させる場合には、例えば、超音波、高剪断力分散やメディア分散等の分散方法により分散させることができる。Examples of the liquid medium in which the light emitting layer material is dissolved or dispersed in the wet method include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene. Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as dimethylformamide (DMF) and dimethylsulfoxide (DMSO) can be used.
Further, when the light emitting layer material is dispersed in the liquid medium, it can be dispersed by a dispersion method such as ultrasonic wave, high shearing force dispersion or media dispersion.
また、発光層の形成方法として蒸着法を採用する場合、その蒸着条件は使用する化合物の種類等により異なるが、一般にボート加熱温度50〜450℃、真空度10−6〜10−2Pa、蒸着速度0.01〜50nm/秒、基板温度−50〜300℃、層厚0.1nm〜5μm、好ましくは5〜200nmの範囲で適宜選ぶことが望ましい。Moreover, when employ | adopting a vapor deposition method as a formation method of a light emitting layer, although the vapor deposition conditions change with kinds etc. of the compound to be used, generally boat heating temperature 50-450 degreeC,
[1.発光ドーパント]
発光ドーパントとしては、蛍光発光性ドーパント(蛍光ドーパント、蛍光性化合物ともいう。)又はリン光発光性ドーパント(リン光ドーパント、リン光性化合物ともいう。)が好ましく用いられる。発光層中の発光ドーパントの濃度については、使用される特定のドーパント及びデバイスの必要条件に基づいて、任意に決定することができる。発光ドーパントの濃度は、発光層の層厚方向に対し、均一な濃度で含有されていてもよいし、任意の濃度分布を有していてもよい。[1. Luminescent dopant]
As the luminescent dopant, a fluorescent luminescent dopant (also referred to as a fluorescent dopant or a fluorescent compound) or a phosphorescent dopant (also referred to as a phosphorescent dopant or a phosphorescent compound) is preferably used. The concentration of the light-emitting dopant in the light-emitting layer can be arbitrarily determined based on the specific dopant used and the device requirements. The concentration of the light-emitting dopant may be contained at a uniform concentration in the thickness direction of the light-emitting layer, or may have an arbitrary concentration distribution.
また、発光層には、複数種の発光ドーパントが含まれていてもよい。例えば、構造の異なるドーパント同士の組み合わせや、蛍光発光性ドーパントとリン光発光性ドーパントとを組み合わせて用いてもよい。これにより、任意の発光色を得ることができる。 The light emitting layer may contain a plurality of types of light emitting dopants. For example, a combination of dopants having different structures, or a combination of a fluorescent luminescent dopant and a phosphorescent luminescent dopant may be used. Thereby, arbitrary luminescent colors can be obtained.
有機EL素子は、1層又は複数層の発光層が、発光色の異なる複数の発光ドーパントを含有し、有機EL素子全体として白色発光を示すことが好ましい。白色を示す発光ドーパントの組み合わせについては特に限定はないが、例えば青と橙との組み合わせや、青と緑と赤との組み合わせ等が挙げられる。有機EL素子における白色としては、2度視野角正面輝度を分光放射輝度計により測定した際に、1000cd/m2でのCIE1931表色系における色度がx=0.39±0.09、y=0.38±0.08の領域内にあることが好ましい。In the organic EL element, it is preferable that one or a plurality of light-emitting layers contain a plurality of light-emitting dopants having different emission colors and emit white light as a whole of the organic EL element. There are no particular limitations on the combination of light-emitting dopants that exhibit white, but examples include a combination of blue and orange, a combination of blue, green, and red. As the white color in the organic EL element, the chromaticity in the CIE 1931 color system at 1000 cd / m 2 is x = 0.39 ± 0.09 when the 2 ° viewing angle front luminance is measured with a spectral radiance meter. = 0.38 ± 0.08 is preferable.
[1−1.リン光発光性ドーパント]
リン光発光性ドーパントは、励起三重項からの発光が観測される化合物であり、具体的には、室温(25℃)にてリン光発光する化合物であり、25℃においてリン光量子収率が0.01以上の化合物である。発光層に用いられるリン光発光性ドーパントにおいて、好ましいリン光量子収率は0.1以上である。[1-1. Phosphorescent dopant]
The phosphorescent dopant is a compound in which light emission from an excited triplet is observed. Specifically, the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 0 at 25 ° C. .01 or more compounds. In the phosphorescent dopant used for a light emitting layer, a preferable phosphorescence quantum yield is 0.1 or more.
上記リン光量子収率は、第4版実験化学講座7の分光IIの398頁(1992年版、丸善)に記載の方法により測定できる。溶液中でのリン光量子収率は種々の溶媒を用いて測定できる。発光層に用いられるリン光発光性ドーパントは、任意の溶媒のいずれかにおいて上記リン光量子収率(0.01以上)が達成されればよい。 The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. The phosphorescence quantum yield in a solution can be measured using various solvents. The phosphorescence emission dopant used for a light emitting layer should just achieve the said phosphorescence quantum yield (0.01 or more) in any arbitrary solvent.
リン光発光性ドーパントは、有機EL素子の発光層に使用される公知の材料から適宜選択して用いることができる。 The phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL element.
中でも、好ましいリン光発光性ドーパントとしては、Irを中心金属に有する有機金属錯体が挙げられる。更に好ましくは、金属−炭素結合、金属−窒素結合、金属−酸素結合、金属−硫黄結合の少なくとも一つの配位様式を含む錯体が好ましい。 Among these, preferable phosphorescent dopants include organometallic complexes having Ir as a central metal. More preferably, a complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is preferable.
[1−2.蛍光発光性ドーパント]
蛍光発光性ドーパントは、励起一重項からの発光が可能な化合物であり、励起一重項からの発光が観測される限り特に限定されない。[1-2. Fluorescent luminescent dopant]
The fluorescent light-emitting dopant is a compound that can emit light from an excited singlet, and is not particularly limited as long as light emission from the excited singlet is observed.
蛍光発光性ドーパントしては、例えば、アントラセン誘導体、ピレン誘導体、クリセン誘導体、フルオランテン誘導体、ペリレン誘導体、フルオレン誘導体、アリールアセチレン誘導体、スチリルアリーレン誘導体、スチリルアミン誘導体、アリールアミン誘導体、ホウ素錯体、クマリン誘導体、ピラン誘導体、シアニン誘導体、クロコニウム誘導体、スクアリウム誘導体、オキソベンツアントラセン誘導体、フルオレセイン誘導体、ローダミン誘導体、ピリリウム誘導体、ペリレン誘導体、ポリチオフェン誘導体、又は希土類錯体系化合物等が挙げられる。 Examples of the fluorescent light-emitting dopant include anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, perylene derivatives, fluorene derivatives, arylacetylene derivatives, styrylarylene derivatives, styrylamine derivatives, arylamine derivatives, boron complexes, coumarin derivatives, Examples include pyran derivatives, cyanine derivatives, croconium derivatives, squalium derivatives, oxobenzanthracene derivatives, fluorescein derivatives, rhodamine derivatives, pyrylium derivatives, perylene derivatives, polythiophene derivatives, rare earth complex compounds, and the like.
また、蛍光発光性ドーパントして、遅延蛍光を利用した発光ドーパント等を用いてもよい。
遅延蛍光を利用した発光ドーパントの具体例としては、例えば、国際公開第2011/156793号、特開2011−213643号公報、特開2010−93181号公報等に記載の化合物が挙げられる。In addition, a light emitting dopant using delayed fluorescence may be used as the fluorescent light emitting dopant.
Specific examples of the luminescent dopant using delayed fluorescence include compounds described in, for example, International Publication No. 2011/156793, Japanese Patent Application Laid-Open No. 2011-213643, Japanese Patent Application Laid-Open No. 2010-93181, and the like.
[2.ホスト化合物]
ホスト化合物は、発光層において主に電荷の注入及び輸送を担う化合物であり、有機EL素子においてそれ自体の発光は実質的に観測されない。
好ましくは室温(25℃)においてリン光発光のリン光量子収率が、0.1未満の化合物であり、更に好ましくは、リン光量子収率が0.01未満の化合物である。また、発光層に含有される化合物の内で、その層中での質量比が20%以上であることが好ましい。[2. Host compound]
The host compound is a compound mainly responsible for charge injection and transport in the light emitting layer, and its own light emission is not substantially observed in the organic EL element.
Preferably, it is a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.1 at room temperature (25 ° C.), more preferably a compound having a phosphorescence quantum yield of less than 0.01. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
また、ホスト化合物の励起状態エネルギーは、同一層内に含有される発光ドーパントの励起状態エネルギーよりも高いことが好ましい。
ホスト化合物は、単独で用いてもよく、又は複数種併用して用いてもよい。ホスト化合物を複数種用いることで、電荷の移動を調整することが可能であり、有機EL素子の高効率化が可能となる。Moreover, it is preferable that the excited state energy of a host compound is higher than the excited state energy of the light emission dopant contained in the same layer.
A host compound may be used independently or may be used in combination of multiple types. By using a plurality of types of host compounds, it is possible to adjust the movement of electric charges, and it is possible to increase the efficiency of the organic EL element.
発光層に用いられるホスト化合物としては、従来有機EL素子で用いられる化合物を用いることができる。例えば、低分子化合物や、繰り返し単位を有する高分子化合物でもよいし、ビニル基やエポキシ基のような反応性基を有する化合物でもよい。 As a host compound used in the light emitting layer, a compound conventionally used in an organic EL device can be used. For example, a low molecular compound, a high molecular compound having a repeating unit, or a compound having a reactive group such as a vinyl group or an epoxy group may be used.
公知のホスト化合物としては、正孔輸送能又は電子輸送能を有しつつ、発光の長波長化を防ぎ、更に、有機EL素子を高温駆動時や素子駆動中の発熱に対する安定性の観点から、高いガラス転移温度(Tg)を有することが好ましい。ホスト化合物としては、Tgが80℃以上であることが好ましく、より好ましくは100℃以上である。
ここで、ガラス転移点(Tg)とは、DSC(Differential Scanning Colorimetry:示差走査熱量法)を用いて、JIS−K−7121に準拠した方法により求められる値である。As a known host compound, while having a hole transport ability or an electron transport ability, it prevents the light emission from becoming longer wavelength, and further, from the viewpoint of stability against heat generation during driving of the organic EL element at high temperature or during element driving, It is preferable to have a high glass transition temperature (Tg). As a host compound, it is preferable that Tg is 80 degreeC or more, More preferably, it is 100 degreeC or more.
Here, a glass transition point (Tg) is a value calculated | required by the method based on JIS-K-7121 using DSC (Differential Scanning Colorimetry: Differential scanning calorimetry).
ただし、発光ドーパントの材料及びホスト化合物の材料としては、後述するように、発光層のホストのIpが発光層のドーパントのIpより0.3eV以上深くなるように選択する。 However, the material of the light emitting dopant and the material of the host compound are selected so that the host Ip of the light emitting layer is 0.3 eV or more deeper than the dopant Ip of the light emitting layer, as will be described later.
本発明の有機EL素子においては、発光層のホスト化合物のIpが発光層の発光ドーパントのIpより0.3eV以上深い。
発光層のホスト化合物のIpを発光層の発光ドーパントのIpより0.3eV以上深くすることで、正孔輸送層側で再結合するため、電子輸送材料の影響を受けにくくなる。これにより、発光効率が向上するとともに、素子寿命が長くなる。In the organic EL device of the present invention, the Ip of the host compound of the light emitting layer is 0.3 eV or more deeper than the Ip of the light emitting dopant of the light emitting layer.
By making the Ip of the host compound of the light emitting layer 0.3 eV or more deeper than the Ip of the light emitting dopant of the light emitting layer, recombination occurs on the hole transport layer side, so that it is less susceptible to the influence of the electron transport material. As a result, the light emission efficiency is improved and the device life is extended.
発光層のホスト化合物のIpの深さが、発光層の発光ドーパントのIpの深さに対して0.3eV未満であると、電子輸送材料の影響を受けやすくなり、発光効率が低下するとともに素子寿命が短くなる。
したがって、発光層のホスト化合物のIpを発光層の発光ドーパントのIpより0.3eV以上深くする。深さの差は、電子輸送材料の影響をより受けにくくする観点から、好ましくは0.5eV以上、より好ましくは0.7eV以上である。When the Ip depth of the host compound in the light emitting layer is less than 0.3 eV with respect to the Ip depth of the light emitting dopant in the light emitting layer, the device is easily affected by the electron transport material, and the light emission efficiency is lowered and the device is reduced. Life is shortened.
Therefore, the Ip of the host compound in the light emitting layer is made 0.3 eV or more deeper than the Ip of the light emitting dopant in the light emitting layer. The difference in depth is preferably 0.5 eV or more, more preferably 0.7 eV or more, from the viewpoint of making it less susceptible to the influence of the electron transport material.
なお、Ipの深さの差の上限については特に規定されないが、バンドギャップおよび電子親和力の設計のしやすさの観点から、好ましくは2.0eV以下、より好ましくは1.5eV以下である。
発光層のホスト化合物を複数含む場合は、発光層の最もIpが浅いホスト化合物のIpを発光層の発光ドーパントのIpより0.3eV以上深くする。また、発光層に発光ドーパントを複数含む場合は、発光層のホスト化合物のIpを発光層の最もIpの深い発光ドーパントのIpより0.3eV以上深くする。The upper limit of the Ip depth difference is not particularly defined, but is preferably 2.0 eV or less, and more preferably 1.5 eV or less, from the viewpoint of ease of designing the band gap and electron affinity.
When a plurality of host compounds are included in the light emitting layer, the Ip of the host compound having the shallowest Ip in the light emitting layer is set to be 0.3 eV or more deeper than the Ip of the light emitting dopant in the light emitting layer. When the light emitting layer includes a plurality of light emitting dopants, the Ip of the host compound in the light emitting layer is set to be 0.3 eV or more deeper than the Ip of the light emitting dopant having the deepest Ip in the light emitting layer.
本発明の有機EL素子においては、極性フッ化溶媒が、各構成層全体として1000質量ppm以下含有されていることが好ましい。この範囲内とすることにより、有機EL素子材料間の電荷授受を損なうことなく、駆動時に発生する熱等のエネルギーにより有機EL素子材料が再配向して結晶粒とならず、結晶粒界の電荷トラップにより輸送性が低下することもない。なお、極性フッ化溶媒は、各構成層全体として100質量ppm以上含有されていることが好ましい。
なお、各構成層全体とは、陽極と陰極との間に形成された層(有機層)全体のことである。
極性フッ化溶媒の詳細については、後述する有機EL素子の製造方法で説明する。In the organic EL device of the present invention, the polar fluorinated solvent is preferably contained in an amount of 1000 ppm by mass or less as the entire constituent layers. By making it within this range, the organic EL element material is reoriented by energy such as heat generated at the time of driving without deteriorating the charge transfer between the organic EL element materials, and the crystal grain boundary charges are not re-oriented. Transportability is not reduced by the trap. In addition, it is preferable that 100 mass ppm or more of polar fluorinated solvents are contained as each whole constituent layer.
In addition, each whole constituent layer is the whole layer (organic layer) formed between the anode and the cathode.
Details of the polar fluorinated solvent will be described in the method for producing an organic EL element described later.
本発明の有機EL素子において、各構成層全体としての極性フッ化溶媒の含有量は、次のようにして測定することができる。
まず、30mm角のガラス基板上に、測定対象の有機EL素子と同様にして、正孔注入層から電子輸送層までの各層を形成したサンプルを作製する。このサンプルの平坦膜部から1cm口程度のサンプルを2つ切り出す。その一方は、トルエンを浸したクリーンワイパーで正孔注入層から電子輸送層までの全層を一部剥ぎ取って段差をつけ、サンユー電子社製SC−701 MkII ECOでAg薄膜をスパッタ後、Veeco社製WYKOを用いて段差を計測し、膜厚を決定する。更に、切り出したもう一方のサンプルは、正孔注入層から電子輸送層までの全層をトルエン浸漬により除去し、除去前後の質量比から膜面積を求める。上記面積が決定されたサンプルを電子科学社製の昇温熱脱離分析装置により測定し、層の形成に使用した極性フッ化溶媒に対応するマスフラグメントスペクトルから、脱離ガス成分を定量し、各有機層積層体の体積当たりの極性フッ化溶媒の質量比を求める。以上のようにして、極性フッ化溶媒の含有量を求めることができる。In the organic EL device of the present invention, the content of the polar fluorinated solvent as a whole of each constituent layer can be measured as follows.
First, the sample which formed each layer from a positive hole injection layer to an electron carrying layer on a 30 mm square glass substrate similarly to the organic EL element of a measuring object is produced. Two samples of about 1 cm mouth are cut out from the flat film portion of this sample. One of them is a part of the whole layer from the hole injection layer to the electron transport layer, which is stripped with a clean wiper soaked in toluene, to make a step, and after sputtering an Ag thin film with SC-701 MkII ECO manufactured by Sanyu Electronics, Veeco The step is measured using WYKO manufactured by KK and the film thickness is determined. Further, in the other sample cut out, the entire layer from the hole injection layer to the electron transport layer is removed by immersion in toluene, and the film area is determined from the mass ratio before and after the removal. The sample whose area was determined was measured with a temperature-programmed thermal desorption analyzer manufactured by Denshi Kagaku Co., and the desorbed gas component was quantified from the mass fragment spectrum corresponding to the polar fluorinated solvent used for forming the layer. The mass ratio of the polar fluorinated solvent per volume of the organic layer laminate is determined. As described above, the content of the polar fluorinated solvent can be determined.
《電子輸送層》
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層も電子輸送層に含まれる。電子輸送層は単層又は複数層設けることができる。
また、電子輸送層は、以下に説明する電子輸送材料を含有する塗布液を用いて形成することが好ましい。また、当該塗布液は極性フッ化溶媒を含有することが好ましい。極性フッ化溶媒に対する溶解度は、電子輸送層の材料、発光層の材料の順に低くなることが好ましい。《Electron transport layer》
The electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, the electron injection layer is also included in the electron transport layer. The electron transport layer can be provided as a single layer or a plurality of layers.
Moreover, it is preferable to form an electron carrying layer using the coating liquid containing the electron carrying material demonstrated below. The coating solution preferably contains a polar fluorinated solvent. The solubility in the polar fluorinated solvent is preferably decreased in the order of the material for the electron transport layer and the material for the light emitting layer.
従来、電子輸送層(複数層とする場合は陰極側に隣接する電子輸送層)に用いられる電子輸送材料としては、陰極より注入された電子を発光層に伝達する機能を有していればよく、その材料としては従来公知の化合物の中から任意のものを選択して用いることができる。例えば、フルオレン誘導体、カルバゾール誘導体、アザカルバゾール誘導体、オキサジアゾール誘導体、トリアゾール誘導体、シロール誘導体、ピリジン誘導体、ピリミジン誘導体、8−キノリノール誘導体等の金属錯体等が挙げられる。 Conventionally, as an electron transport material used for an electron transport layer (in the case of a plurality of layers, an electron transport layer adjacent to the cathode side), it is only necessary to have a function of transmitting electrons injected from the cathode to the light emitting layer. As the material, any one of conventionally known compounds can be selected and used. Examples thereof include metal complexes such as a fluorene derivative, a carbazole derivative, an azacarbazole derivative, an oxadiazole derivative, a triazole derivative, a silole derivative, a pyridine derivative, a pyrimidine derivative, and an 8-quinolinol derivative.
その他、メタルフリー若しくはメタルフタロシアニン、又はそれらの末端がアルキル基やスルホン酸基等で置換されているものも、電子輸送材料として好ましく用いることができる。
これらの中でもカルバゾール誘導体、アザカルバゾール誘導体、ピリジン誘導体等が本発明では好ましく、アザカルバゾール誘導体であることがより好ましい。In addition, metal-free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transport material.
Among these, a carbazole derivative, an azacarbazole derivative, a pyridine derivative, and the like are preferable in the present invention, and an azacarbazole derivative is more preferable.
電子輸送層は、上記電子輸送材料を、例えば、ダイコート法、ブレードコート法、ロールコート法、スプレーコート法、カーテンコート法、スピンコート法、キャスト法、インクジェット法を含む印刷法、LB法等の公知の方法により、薄膜化することにより形成することができ、好ましくは上記電子輸送材料、フッ化アルコール溶剤とを含有する塗布液を用いたウェットプロセスにより形成することができる。 The electron transport layer is formed by using the above electron transport material, for example, a die coating method, a blade coating method, a roll coating method, a spray coating method, a curtain coating method, a spin coating method, a casting method, a printing method including an inkjet method, an LB method, or the like. It can be formed by thinning by a known method, preferably by a wet process using a coating solution containing the electron transport material and the fluorinated alcohol solvent.
電子輸送層の層厚については特に制限はないが、通常は5nm〜5μm程度、好ましくは5〜200nmである。電子輸送層は上記材料の1種又は2種以上からなる一層構造であってもよい。 Although there is no restriction | limiting in particular about the layer thickness of an electron carrying layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.
また、上記電子輸送材料の他に、不純物をゲスト材料としてドープしたn性の高い電子輸送層を用いることもできる。その例としては、特開平4−297076号公報、同10−270172号公報、特開2000−196140号公報、同2001−102175号公報、J.Appl.Phys.,95,5773(2004)等に記載されたものが挙げられる。 In addition to the electron transport material, an electron transport layer having high n property in which an impurity is doped as a guest material can also be used. Examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
本発明における電子輸送層には、有機物のアルカリ金属塩を含有することが好ましい。有機物の種類としては特に制限はないが、ギ酸塩、酢酸塩、プロピオン酸塩、酪酸塩、吉草酸塩、カプロン酸塩、エナント酸塩、カプリル酸塩、シュウ酸塩、マロン酸塩、コハク酸塩、安息香酸塩、フタル酸塩、イソフタル酸塩、テレフタル酸塩、サリチル酸塩、ピルビン酸塩、乳酸塩、リンゴ酸塩、アジピン酸塩、メシル酸塩、トシル酸塩、ベンゼンスルホン酸塩が挙げられ、好ましくはギ酸塩、酢酸塩、プロピオン酸塩、酪酸塩、吉草酸塩、カプロン酸塩、エナント酸塩、カプリル酸塩、シュウ酸塩、マロン酸塩、コハク酸塩、安息香酸塩、より好ましくはギ酸塩、酢酸塩、プロピオン酸塩、酪酸塩等の脂肪族カルボン酸のアルカリ金属塩が好ましく、脂肪族カルボン酸の炭素原子数が4以下であることが好ましい。最も好ましくは酢酸塩である。 The electron transport layer in the present invention preferably contains an organic alkali metal salt. There are no particular restrictions on the type of organic substance, but formate, acetate, propionate, butyrate, valerate, caprate, enanthate, caprylate, oxalate, malonate, succinic acid Salt, benzoate, phthalate, isophthalate, terephthalate, salicylate, pyruvate, lactate, malate, adipate, mesylate, tosylate, benzenesulfonate Preferably, formate, acetate, propionate, butyrate, valerate, caprate, enanthate, caprylate, oxalate, malonate, succinate, benzoate, and more Preferred are alkali metal salts of aliphatic carboxylic acids such as formate, acetate, propionate, butyrate, etc., and the number of carbon atoms of the aliphatic carboxylic acid is preferably 4 or less. Most preferred is acetate.
有機物のアルカリ金属塩のアルカリ金属の種類としては特に制限はないが、Na、K、Cs、Liが挙げられ、好ましくはK、Cs、更に好ましくはCsである。有機物のアルカリ金属塩としては、前記有機物とアルカリ金属の組み合わせが挙げられ、好ましくは、ギ酸Li、ギ酸K、ギ酸Na、ギ酸Cs、酢酸Li、酢酸K、酢酸Na、酢酸Cs、プロピオン酸Li、プロピオン酸Na、プロピオン酸K、プロピオン酸Cs、シュウ酸Li、シュウ酸Na、シュウ酸K、シュウ酸Cs、マロン酸Li、マロン酸Na、マロン酸K、マロン酸Cs、コハク酸Li、コハク酸Na、コハク酸K、コハク酸Cs、安息香酸Li、安息香酸Na、安息香酸K、安息香酸Cs、より好ましくは酢酸Li、酢酸K、酢酸Na、酢酸Cs、最も好ましくは酢酸Csである。
これらドープ材の含有量は、添加する電子輸送層に対し、好ましくは1.5〜35質量%であり、より好ましくは3〜25質量%であり、最も好ましくは5〜15質量%である。The kind of alkali metal of the organic alkali metal salt is not particularly limited, and examples thereof include Na, K, Cs, and Li, preferably K, Cs, and more preferably Cs. Examples of the alkali metal salt of the organic substance include a combination of the organic substance and the alkali metal, preferably, formic acid Li, formic acid K, Na formic acid, formic acid Cs, Li acetate, K acetate, Na acetate, Cs acetate, Lipropionate, Propionic acid Na, propionic acid K, propionic acid Cs, oxalic acid Li, oxalic acid Na, oxalic acid K, oxalic acid Cs, malonic acid Li, malonic acid Na, malonic acid K, malonic acid Cs, succinic acid Li, succinic acid Na, succinic acid K, succinic acid Cs, benzoic acid Li, benzoic acid Na, benzoic acid K, benzoic acid Cs, more preferably Li acetate, K acetate, Na acetate, Cs acetate, most preferably Cs acetate.
The content of these dope materials is preferably 1.5 to 35% by mass, more preferably 3 to 25% by mass, and most preferably 5 to 15% by mass with respect to the electron transport layer to be added.
ただし、電子輸送層の材料としては、後述するように、電子輸送層に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上となるように選択する。 However, the material for the electron transport layer is selected so that the molecular dipole moment of at least one organic compound contained in the electron transport layer is 6.0 debye or more, as will be described later.
本発明の有機EL素子においては、電子輸送層に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上である。
有機化合物の分子双極子モーメントを6.0デバイ以上とすることで、界面電界により注入障壁が緩和され、低電圧化を図ることができる。
したがって、前記有機化合物の分子双極子モーメントは6.0デバイ以上とする。注入障壁をより緩和する観点から、好ましくは8.0デバイ以上、より好ましくは10.0デバイ以上、更に好ましくは12.0デバイ以上である。
なお、有機化合物の分子双極子モーメントの上限については特に規定されないが、結晶化および溶媒残留の観点から、好ましくは16.0デバイ以下、より好ましくは14.0デバイ以下である。In the organic EL device of the present invention, the molecular dipole moment of at least one organic compound contained in the electron transport layer is 6.0 debye or more.
By setting the molecular dipole moment of the organic compound to 6.0 debyes or more, the injection barrier is relaxed by the interface electric field, and the voltage can be reduced.
Therefore, the molecular dipole moment of the organic compound is 6.0 debye or more. From the viewpoint of further relaxing the injection barrier, it is preferably 8.0 debye or more, more preferably 10.0 debye or more, and further preferably 12.0 debye or more.
The upper limit of the molecular dipole moment of the organic compound is not particularly defined, but is preferably 16.0 debye or less, more preferably 14.0 debye or less from the viewpoint of crystallization and solvent residue.
前記有機化合物は、例えば、下記一般式(1)で表される化合物とすることができる。 The organic compound can be, for example, a compound represented by the following general formula (1).
一般式(1)中、Z1とZ2は、各々独立に、置換基を有していてもよい、6員の芳香族炭化水素環又は6員の芳香族複素環を表し、Z3は単なる結合手を表す。また、一般式(1)中、R101は置換基を有していてもよいアリール基又は置換基を有していてもよい芳香族複素環基を表す。In General Formula (1), Z 1 and Z 2 each independently represent a 6-membered aromatic hydrocarbon ring or 6-membered aromatic heterocycle, which may have a substituent, and Z 3 represents Represents a simple bond. In the general formula (1), R 101 represents an aryl group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
前記一般式(1)において、Z1、Z2で表される6員の芳香族炭化水素環としては、ベンゼン環、ビフェニル環、ナフタレン環、アズレン環、アントラセン環、フェナントレン環、ピレン環、クリセン環、ナフタセン環、トリフェニレン環、o−テルフェニル環、m−テルフェニル環、p−テルフェニル環、アセナフテン環、コロネン環、フルオレン環、フルオラントレン環、ナフタセン環、ペンタセン環、ペリレン環、ペンタフェン環、ピセン環、ピレン環、ピラントレン環及びアンスラアントレン環等が挙げられる。更に、前記6員の芳香族炭化水素環は、後述するR101で表される置換基が置換基として有してもよい置換基群Aを有してもよい。In the general formula (1), the 6-membered aromatic hydrocarbon ring represented by Z 1 or Z 2 includes a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene Ring, naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen And a ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthraanthrene ring. Furthermore, the 6-membered aromatic hydrocarbon ring may have a substituent group A that a substituent represented by R 101 described later may have as a substituent.
前記一般式(1)において、Z1、Z2で表される6員の芳香族複素環としては、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、トリアジン環、キノキサリン環、カルボリン環、カルボリン環を構成する炭化水素環の炭素原子が更に窒素原子で置換されている環等が挙げられる。更に、前記6員の芳香族複素環は、後述するR101で表される置換基が置換基として有してもよい置換基群Aを有してもよい。In the general formula (1), examples of the 6-membered aromatic heterocycle represented by Z 1 or Z 2 include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a quinoxaline ring, a carboline ring, and a carboline ring. And a ring in which the carbon atom of the hydrocarbon ring constituting is further substituted with a nitrogen atom. Furthermore, aromatic heterocycle of the 6-membered, substituents represented by R 101 to be described later may have a substituent group A which may have a substituent.
前記一般式(1)中、Z1が置換基を有していてもよいピリジン環を表し、Z2が置換基を有していてもよいベンゼン環を表すことが好ましい。
あるいは、前記一般式(1)中、Z1及びZ2が置換基を有していてもよいピリジン環を表すことが好ましい。
これらの構成であれば、窒素原子上の高い電子密度により求核性および分子内ダイポールをより強く発現できるため、良好な電子注入輸送材となる。In the general formula (1), Z 1 preferably represents a pyridine ring which may have a substituent, and Z 2 preferably represents a benzene ring which may have a substituent.
Alternatively, in the general formula (1), it is preferable that Z 1 and Z 2 represents a pyridine ring optionally having a substituent.
With these structures, nucleophilicity and intramolecular dipoles can be more strongly expressed by a high electron density on the nitrogen atom, so that it becomes a good electron injecting and transporting material.
また、一般式(1)で表される化合物が、炭素と窒素と水素のみから成るものであることが好ましい。
このような構成であれば、分子配列の異方性が強くなり、より良好な電子注入輸送材になる。Moreover, it is preferable that the compound represented by General formula (1) consists only of carbon, nitrogen, and hydrogen.
With such a configuration, the anisotropy of the molecular arrangement becomes strong and a better electron injecting and transporting material is obtained.
一般式(1)において、R101で表される置換基としては、アリール基(例えば、フェニル基、ナフチル基等)、芳香族複素環基(例えば、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、ピラゾリル基、チアゾリル基、キナゾリニル基、フタラジニル基等)等が挙げられる。In the general formula (1), examples of the substituent represented by R 101 include an aryl group (eg, phenyl group, naphthyl group, etc.), an aromatic heterocyclic group (eg, furyl group, thienyl group, pyridyl group, pyridazinyl group). , Pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthalazinyl group, and the like.
これらのR101で表される置換基は、下記の置換基群Aによって更に置換されていてもよい。また、これらの置換基は複数が互いに結合して環を形成していてもよい。These substituents represented by R 101 may be further substituted by the following substituent group A. In addition, a plurality of these substituents may be bonded to each other to form a ring.
置換基群Aとしては、アルキル基(例えば、メチル基、エチル基、プロピル基、イソプロピル基、tert−ブチル基、ペンチル基、ヘキシル基、オクチル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基等)、シクロアルキル基(例えば、シクロペンチル基、シクロヘキシル基等)、アルケニル基(例えば、ビニル基、アリル基等)、アルキニル基(例えば、エチニル基、プロパルギル基等)、アリール基(例えば、フェニル基、ナフチル基等)、芳香族複素環基(例えば、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、ピラゾリル基、チアゾリル基、キナゾリニル基、フタラジニル基等)、複素環基(例えば、ピロリジル基、イミダゾリジル基、モルホリル基、オキサゾリジル基等)、アルコキシル基(例えば、メトキシ基、エトキシ基、プロピルオキシ基、ペンチルオキシ基、ヘキシルオキシ基、オクチルオキシ基、ドデシルオキシ基等)、シクロアルコキシル基(例えば、シクロペンチルオキシ基、シクロヘキシルオキシ基等)、アリールオキシ基(例えば、フェノキシ基、ナフチルオキシ基等)、アルキルチオ基(例えば、メチルチオ基、エチルチオ基、プロピルチオ基、ペンチルチオ基、ヘキシルチオ基、オクチルチオ基、ドデシルチオ基等)、シクロアルキルチオ基(例えば、シクロペンチルチオ基、シクロヘキシルチオ基等)、アリールチオ基(例えば、フェニルチオ基、ナフチルチオ基等)、アルコキシカルボニル基(例えば、メチルオキシカルボニル基、エチルオキシカルボニル基、ブチルオキシカルボニル基、オクチルオキシカルボニル基、ドデシルオキシカルボニル基等)、アリールオキシカルボニル基(例えば、フェニルオキシカルボニル基、ナフチルオキシカルボニル基等)、スルファモイル基(例えば、アミノスルホニル基、メチルアミノスルホニル基、ジメチルアミノスルホニル基、ブチルアミノスルホニル基、ヘキシルアミノスルホニル基、シクロヘキシルアミノスルホニル基、オクチルアミノスルホニル基、ドデシルアミノスルホニル基、フェニルアミノスルホニル基、ナフチルアミノスルホニル基、2−ピリジルアミノスルホニル基等)、アシル基(例えば、アセチル基、エチルカルボニル基、プロピルカルボニル基、ペンチルカルボニル基、シクロヘキシルカルボニル基、オクチルカルボニル基、2−エチルヘキシルカルボニル基、ドデシルカルボニル基、フェニルカルボニル基、ナフチルカルボニル基、ピリジルカルボニル基等)、アシルオキシ基(例えば、アセチルオキシ基、エチルカルボニルオキシ基、ブチルカルボニルオキシ基、オクチルカルボニルオキシ基、ドデシルカルボニルオキシ基、フェニルカルボニルオキシ基等)、アミド基(例えば、メチルカルボニルアミノ基、エチルカルボニルアミノ基、ジメチルカルボニルアミノ基、プロピルカルボニルアミノ基、ペンチルカルボニルアミノ基、シクロヘキシルカルボニルアミノ基、2−エチルヘキシルカルボニルアミノ基、オクチルカルボニルアミノ基、ドデシルカルボニルアミノ基、フェニルカルボニルアミノ基、ナフチルカルボニルアミノ基等)、カルバモイル基(例えば、アミノカルボニル基、メチルアミノカルボニル基、ジメチルアミノカルボニル基、プロピルアミノカルボニル基、ペンチルアミノカルボニル基、シクロヘキシルアミノカルボニル基、オクチルアミノカルボニル基、2−エチルヘキシルアミノカルボニル基、ドデシルアミノカルボニル基、フェニルアミノカルボニル基、ナフチルアミノカルボニル基、2−ピリジルアミノカルボニル基等)、ウレイド基(例えば、メチルウレイド基、エチルウレイド基、ペンチルウレイド基、シクロヘキシルウレイド基、オクチルウレイド基、ドデシルウレイド基、フェニルウレイド基、ナフチルウレイド基、2−ピリジルアミノウレイド基等)、スルフィニル基(例えば、メチルスルフィニル基、エチルスルフィニル基、ブチルスルフィニル基、シクロヘキシルスルフィニル基、2−エチルヘキシルスルフィニル基、ドデシルスルフィニル基、フェニルスルフィニル基、ナフチルスルフィニル基、2−ピリジルスルフィニル基等)、アルキルスルホニル基(例えば、メチルスルホニル基、エチルスルホニル基、ブチルスルホニル基、シクロヘキシルスルホニル基、2−エチルヘキシルスルホニル基、ドデシルスルホニル基等)、アリールスルホニル基(フェニルスルホニル基、ナフチルスルホニル基、2−ピリジルスルホニル基等)、アミノ基(例えば、アミノ基、エチルアミノ基、ジメチルアミノ基、ブチルアミノ基、シクロペンチルアミノ基、2−エチルヘキシルアミノ基、ドデシルアミノ基、アニリノ基、ナフチルアミノ基、2−ピリジルアミノ基等)、ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子等)、フッ化炭化水素基(例えば、フルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、ペンタフルオロフェニル基等)、シアノ基、ニトロ基、ヒドロキシ基、メルカプト基、シリル基(例えば、トリメチルシリル基、トリイソプロピルシリル基、トリフェニルシリル基、フェニルジエチルシリル基等)等が挙げられる。 As the substituent group A, an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc. ), Cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (for example, vinyl group, allyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), aryl group (for example, phenyl group, Naphthyl group, etc.), aromatic heterocyclic groups (for example, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthalazinyl group, etc.) , Heterocyclic groups (eg, pyrrolidyl group, imidazolidyl , Morpholyl group, oxazolidyl group, etc.), alkoxyl group (eg, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (eg, cyclopentyloxy group) Group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.) , Cycloalkylthio group (for example, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (for example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (for example, methyloxycarbonyl group, ethyl group) Sicarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, methyl) Aminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc. ), Acyl groups (eg, acetyl, ethylcarbonyl, propylcarbonyl, pentylcarbonyl, cyclohexylcarbonyl, octylca) Rubonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group (for example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group) , Dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2- Ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carba Yl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group) , Phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido) Group, naphthylureido group, 2-pyridylaminoureido group, etc.), sulfinyl group (for example, methylsulfinyl group, ethylsulfinyl group, butylsulfite) Group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group) Cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc., arylsulfonyl group (phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group etc.), amino group (for example, amino group, ethylamino group, dimethyl) Amino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen atom (example) For example, fluorine atom, chlorine atom, bromine atom, etc.), fluorinated hydrocarbon group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, nitro group, hydroxy group , Mercapto group, silyl group (for example, trimethylsilyl group, triisopropylsilyl group, triphenylsilyl group, phenyldiethylsilyl group, etc.).
好ましい置換基としては、アルキル基、シクロアルキル基、フッ化炭化水素基、アリール基、芳香族複素環基である。 Preferred substituents are an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, and an aromatic heterocyclic group.
Z3で表される単なる結合手とは、連結する置換基同士を直接結合する結合手である。The simple bond represented by Z 3 is a bond that directly bonds the connecting substituents together.
本発明においては、前記一般式(1)のZ1が6員環であることが特徴である。これにより、より発光効率を高くすることができる。更に、より一層長寿命化させることができる。In the present invention, Z 1 in the general formula (1) is a 6-membered ring. Thereby, luminous efficiency can be made higher. Furthermore, the lifetime can be further increased.
また、本発明においては、前記一般式(1)のZ2が6員環であることが特徴である。これにより、より発光効率を高くすることができる。更に、より一層長寿命化させることができる。In the present invention, Z 2 in the general formula (1) is a 6-membered ring. Thereby, luminous efficiency can be made higher. Furthermore, the lifetime can be further increased.
以下、本発明に用いる、電子輸送層に含まれる少なくとも1つの有機化合物の具体例を示すが、これらに限られるものではない。なお、表中、分子双極子モーメントの値は、小数点第2位を四捨五入した値である。 Hereinafter, although the specific example of the at least 1 organic compound contained in an electron carrying layer used for this invention is shown, it is not restricted to these. In the table, the value of the molecular dipole moment is a value obtained by rounding off the second decimal place.
《正孔輸送層》
正孔輸送層は、正孔を輸送する機能を有する正孔輸送材料から構成されており、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。また、正孔輸送層は、単層又は複数層設けることができる。《Hole transport layer》
The hole transport layer is composed of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. Moreover, a positive hole transport layer can be provided in single layer or multiple layers.
正孔輸送材料としては、正孔の注入又は輸送、電子の障壁性のいずれかを有するものであり、有機物、無機物のいずれであってもよい。例えば、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体、ピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、導電性高分子オリゴマー及びチオフェンオリゴマー等が挙げられる。 The hole transport material has any of hole injection or transport and electron barrier properties, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples include stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, and thiophene oligomers.
正孔輸送材料としては、上記のものを使用することができるが、ポルフィリン化合物、芳香族第3級アミン化合物及びスチリルアミン化合物を用いることができ、特に芳香族第3級アミン化合物を用いることが好ましい。 As the hole transport material, those described above can be used, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds can be used, and in particular, aromatic tertiary amine compounds can be used. preferable.
芳香族第3級アミン化合物及びスチリルアミン化合物の代表例としては、N,N,N′,N′−テトラフェニル−4,4′−ジアミノフェニル、N,N′−ジフェニル−N,N′−ビス(3−メチルフェニル)−〔1,1′−ビフェニル〕−4,4′−ジアミン(略称:TPD)、2,2−ビス(4−ジ−p−トリルアミノフェニル)プロパン、1,1−ビス(4−ジ−p−トリルアミノフェニル)シクロヘキサン、N,N,N′,N′−テトラ−p−トリル−4,4′−ジアミノビフェニル、1,1−ビス(4−ジ−p−トリルアミノフェニル)−4−フェニルシクロヘキサン、ビス(4−ジメチルアミノ−2−メチルフェニル)フェニルメタン、ビス(4−ジ−p−トリルアミノフェニル)フェニルメタン、N,N′−ジフェニル−N,N′−ジ(4−メトキシフェニル)−4,4′−ジアミノビフェニル、N,N,N′,N′−テトラフェニル−4,4′−ジアミノジフェニルエーテル、4,4′−ビス(ジフェニルアミノ)クオードリフェニル、N,N,N−トリ(p−トリル)アミン、4−(ジ−p−トリルアミノ)−4′−〔4−(ジ−p−トリルアミノ)スチリル〕スチルベン、4−N,N−ジフェニルアミノ−(2−ジフェニルビニル)ベンゼン、3−メトキシ−4′−N,N−ジフェニルアミノスチルベンゼン及びN−フェニルカルバゾール等が挙げられる。更には米国特許第5061569号明細書に記載されている2個の縮合芳香族環を分子内に有するもの、例えば、4,4′−ビス〔N−(1−ナフチル)−N−フェニルアミノ〕ビフェニル(略称:NPD)、特開平4−308688号公報に記載されているトリフェニルアミンユニットが三つスターバースト型に連結された4,4′,4″−トリス〔N−(3−メチルフェニル)−N−フェニルアミノ〕トリフェニルアミン(略称:MTDATA)等が挙げられる。 Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1 -Bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N ', N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis (4-di-p -Tolylaminophenyl) -4-phenylcyclohexane, bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p-tolylaminophenyl) phenylmethane, N, N'-diphenyl-N, '-Di (4-methoxyphenyl) -4,4'-diaminobiphenyl, N, N, N', N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis (diphenylamino) c Audriphenyl, N, N, N-tri (p-tolyl) amine, 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene, 4-N, N- Examples include diphenylamino- (2-diphenylvinyl) benzene, 3-methoxy-4′-N, N-diphenylaminostilbenzene, N-phenylcarbazole and the like. Furthermore, those having two condensed aromatic rings described in US Pat. No. 5,061,569 in the molecule, for example, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] Biphenyl (abbreviation: NPD), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) in which triphenylamine units described in JP-A-4-308688 are linked in a three star burst type ) -N-phenylamino] triphenylamine (abbreviation: MTDATA).
更に、これらの材料を高分子鎖に導入した、又はこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。また、p型−Si、p型−SiC等の無機化合物も正孔注入材料、正孔輸送材料として使用することができる。 Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
また、特開平11−251067号公報、J.Huang et.al.,Applied Physics Letters,80(2002),p.139に記載されているような、いわゆるp型正孔輸送材料を用いることもできる。本発明においては、より高効率の発光素子が得られる観点から、これらの材料を用いることが好ましい。 JP-A-11-251067, J. Org. Huang et. al. , Applied Physics Letters, 80 (2002), p. A so-called p-type hole transport material as described in 139 can also be used. In the present invention, these materials are preferably used from the viewpoint of obtaining a light-emitting element with higher efficiency.
正孔輸送層は、上記正孔輸送材料を、例えば、真空蒸着法、ダイコート法、ブレードコート法、ロールコート法、スプレーコート法、カーテンコート法、スピンコート法、キャスト法、インクジェット法を含む印刷法、LB法等の公知の方法により、薄膜化することにより形成することができる。正孔輸送層の層厚については特に制限はないが、通常は5nm〜5μm程度、好ましくは5〜200nmの範囲内である。この正孔輸送層は、上記材料の一種又は二種以上からなる一層構造であってもよい。 The hole transport layer is formed by printing the hole transport material including, for example, a vacuum deposition method, a die coating method, a blade coating method, a roll coating method, a spray coating method, a curtain coating method, a spin coating method, a casting method, and an inkjet method. The thin film can be formed by a known method such as the LB method or the LB method. Although there is no restriction | limiting in particular about the layer thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it exists in the range of 5-200 nm. The hole transport layer may have a single layer structure composed of one or more of the above materials.
また、正孔輸送層の材料に不純物をドープすることにより、p性を高くすることもできる。その例としては、特開平4−297076号公報、特開2000−196140号公報、同2001−102175号公報及びJ.Appl.Phys.,95,5773(2004)等に記載されたものが挙げられる。 Moreover, p property can also be made high by doping the material of a positive hole transport layer with an impurity. Examples thereof include JP-A-4-297076, JP-A-2000-196140, 2001-102175 and J.P. Appl. Phys. 95, 5773 (2004), and the like.
このように、正孔輸送層のp性を高くすると、より低消費電力の素子を作製することができるため好ましい。 Thus, it is preferable to increase the p property of the hole transport layer because an element with lower power consumption can be manufactured.
《注入層》
注入層(正孔注入層及び電子注入層)とは、駆動電圧低下や発光輝度向上のために、電極と発光層の間に設けられる層のことで、「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の第2編第2章「電極材料」(123〜166頁)にその詳細が記載されており、正孔注入層と電子注入層とがある。<Injection layer>
An injection layer (a hole injection layer and an electron injection layer) is a layer provided between an electrode and a light-emitting layer in order to reduce drive voltage or improve light emission luminance. The details are described in Chapter 2, “Electrode Materials” (pp. 123-166) of Volume 2 of “November 30, 1998, issued by NTS Corporation”. There is.
注入層は、必要に応じて設けることができる。正孔注入層であれば、アノードと発光層又は正孔輸送層との間、電子注入層であればカソードと発光層又は電子輸送層との間に存在させてもよい。 The injection layer can be provided as necessary. If it is a hole injection layer, it may be present between the anode and the light emitting layer or the hole transport layer, and if it is an electron injection layer, it may be present between the cathode and the light emitting layer or the electron transport layer.
正孔注入層は、特開平9−45479号公報、同9−260062号公報、同8−288069号公報等にその詳細が記載されており、具体例として、銅フタロシアニンに代表されるフタロシアニン層、酸化バナジウムに代表される酸化物層、アモルファスカーボン層、ポリアニリン(エメラルディン)やポリチオフェン等の導電性高分子を用いた高分子層等が挙げられる。 The details of the hole injection layer are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069, and the like. As specific examples, a phthalocyanine layer represented by copper phthalocyanine, Examples thereof include an oxide layer typified by vanadium oxide, an amorphous carbon layer, and a polymer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
電子注入層は、特開平6−325871号公報、同9−17574号公報、同10−74586号公報等にその詳細が記載されており、具体的にはストロンチウムやアルミニウム等に代表される金属層、フッ化カリウムに代表されるアルカリ金属ハライド層、フッ化マグネシウムに代表されるアルカリ土類金属化合物層、酸化モリブデンに代表される酸化物層等が挙げられる。本発明においては、電子注入層はごく薄い膜であることが望ましく、構成材料にもよるが、その層厚は1nm〜10μmの範囲が好ましい。 The details of the electron injection layer are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, a metal layer represented by strontium, aluminum, or the like. And an alkali metal halide layer typified by potassium fluoride, an alkaline earth metal compound layer typified by magnesium fluoride, and an oxide layer typified by molybdenum oxide. In the present invention, the electron injection layer is preferably a very thin film, and although depending on the constituent material, the layer thickness is preferably in the range of 1 nm to 10 μm.
《電子阻止層》
電子阻止層とは、広い意味では、正孔輸送層の機能を有する。電子阻止層は、正孔を輸送する機能を有しつつ、電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔の再結合確率を向上させることができる。また、正孔輸送層の構成を必要に応じて電子阻止層として用いることができる。本発明に適用する正孔阻止層の層厚としては、好ましくは3〜100nmの範囲であり、更に好ましくは5〜30nmの範囲である。《Electron blocking layer》
The electron blocking layer has a function of a hole transport layer in a broad sense. The electron blocking layer is made of a material that has the ability to transport holes and has a very small ability to transport electrons. By blocking holes while transporting holes, the probability of recombination of electrons and holes is improved. Can be made. Moreover, the structure of a positive hole transport layer can be used as an electron blocking layer as needed. The layer thickness of the hole blocking layer applied to the present invention is preferably in the range of 3 to 100 nm, and more preferably in the range of 5 to 30 nm.
《陽極》
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウム・スズ酸化物(ITO)、SnO2、ZnO、IZO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、パターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。また、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等の湿式製膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に、膜厚は材料にもよるが、通常10〜1000nmの範囲内、好ましくは10〜200nmの範囲内で選ばれる。"anode"
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , ZnO, and IZO. Alternatively, an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used. For the anode, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method. When pattern accuracy is not so required (about 100 μm or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material. Moreover, when using the substance which can be apply | coated like an organic electroconductivity compound, wet film forming methods, such as a printing system and a coating system, can also be used. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually selected within the range of 10 to 1000 nm, preferably within the range of 10 to 200 nm.
《陰極》
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する。)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、アルミニウム、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm〜5μmの範囲内、好ましくは50〜200nmの範囲内で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。"cathode"
On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include aluminum, sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably in the range of 50 to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient.
また、陰極に上記金属を1〜20nmの膜厚で作製した後に、陽極の説明で挙げた導電性透明材料をその上に作製することで、透明又は半透明の陰極を作製することができ、これを応用することで陽極と陰極の両方が透過性を有する素子を作製することができる。 Moreover, after producing the metal with a film thickness of 1 to 20 nm on the cathode, a transparent or translucent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode, By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
《基材》
有機EL素子に用いられる基材の材料には特に限定はなく、好ましくは、例えば、ガラス、石英又は樹脂フィルム等を挙げることができる。特に好ましくは、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。"Base material"
There is no limitation in particular in the material of the base material used for an organic EL element, Preferably, glass, quartz, a resin film etc. can be mentioned, for example. Particularly preferred is a resin film capable of giving flexibility to the organic EL element.
樹脂フィルムとしては、例えば、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート(PEN)等のポリエステル、ポリエチレン、ポリプロピレン、セロファン、セルロースジアセテート、セルローストリアセテート(TAC)、セルロースアセテートブチレート、セルロースアセテートプロピオネート(CAP)、セルロースアセテートフタレート、セルロースナイトレート等のセルロースエステル類又はそれらの誘導体、ポリ塩化ビニリデン、ポリビニルアルコール、ポリエチレンビニルアルコール、シンジオタクティックポリスチレン、ポリカーボネート、ノルボルネン樹脂、ポリメチルペンテン、ポリエーテルケトン、ポリイミド、ポリエーテルスルホン(PES)、ポリフェニレンスルフィド、ポリスルホン類、ポリエーテルイミド、ポリエーテルケトンイミド、ポリアミド、フッ素樹脂、ナイロン、ポリメチルメタクリレート、アクリル又はポリアリレート類、アートン(商品名、JSR社製)又はアペル(商品名、三井化学社製)といったシクロオレフィン系樹脂等のフィルムが挙げられる。 Examples of the resin film include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate (TAC), cellulose acetate butyrate, and cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones, Cycloolefins such as polyether imide, polyether ketone imide, polyamide, fluororesin, nylon, polymethyl methacrylate, acrylic or polyarylate, arton (trade name, manufactured by JSR) or appel (trade name, manufactured by Mitsui Chemicals) Examples thereof include a resin film.
樹脂フィルムの表面には、無機物若しくは有機物の被膜又はその両者のハイブリッド被膜等によるガスバリアー膜が形成されていてもよい。ガスバリアー膜は、JIS K 7129−1992に準拠した方法で測定された水蒸気透過度(25±0.5℃、湿度(90±2)%RH)が0.01g/(m2・24h)以下のガスバリアー性フィルムであることが好ましい。更には、JIS K 7126−1987に準拠した方法で測定された酸素透過度が、1×10−3mL/(m2・24h・atm)以下、水蒸気透過度が、1×10−5g/(m2・24h)以下の高ガスバリアー性フィルムであることが好ましい。A gas barrier film may be formed on the surface of the resin film using an inorganic or organic coating or a hybrid coating of both. The gas barrier membrane has a water vapor permeability (25 ± 0.5 ° C., humidity (90 ± 2)% RH) measured by a method according to JIS K 7129-1992 of 0.01 g / (m 2 · 24 h) or less. It is preferable that it is a gas barrier film. Furthermore, the oxygen permeability measured by a method according to JIS K 7126-1987 is 1 × 10 −3 mL / (m 2 · 24 h · atm) or less, and the water vapor permeability is 1 × 10 −5 g / A high gas barrier film of (m 2 · 24 h) or less is preferable.
ガスバリアー膜を形成する材料としては、水分や酸素等の浸入を抑制する機能を有する材料であればよい。例えば、酸化ケイ素、二酸化ケイ素、窒化ケイ素等を用いることができる。更に、ガスバリアー膜の脆弱性を改良するために、これら無機層と有機材料からなる層との積層構造を持たせることがより好ましい。無機層と有機層の積層順については特に制限はないが、両者を交互に複数回積層させることが好ましい。 As a material for forming the gas barrier film, any material having a function of suppressing entry of moisture, oxygen, or the like may be used. For example, silicon oxide, silicon dioxide, silicon nitride, or the like can be used. Furthermore, in order to improve the brittleness of the gas barrier film, it is more preferable to have a laminated structure of these inorganic layers and layers made of organic materials. Although there is no restriction | limiting in particular about the lamination | stacking order of an inorganic layer and an organic layer, It is preferable to laminate | stack both alternately several times.
ガスバリアー膜の形成方法については特に限定はなく、例えば、真空蒸着法、スパッタリング法、反応性スパッタリング法、分子線エピタキシー法、クラスターイオンビーム法、イオンプレーティング法、プラズマ重合法、大気圧プラズマ重合法、プラズマCVD法、レーザーCVD法、熱CVD法、コーティング法等を用いることができる。例えば、特開2004−68143号公報に記載されているような大気圧プラズマ重合法によるものが好ましい。 The method for forming the gas barrier film is not particularly limited. For example, the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used. For example, an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is preferable.
《封止》
本発明の有機EL素子の封止に用いられる封止手段としては、例えば、封止部材と、電極、支持基板とを接着剤で接着する方法を挙げることができる。<Sealing>
Examples of the sealing means used for sealing the organic EL element of the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
封止部材としては、有機EL素子の表示領域を覆うように配置されていればよく、凹板状でも、平板状でもよい。また、透明性、電気絶縁性は特に限定されない。 As a sealing member, it should just be arrange | positioned so that the display area | region of an organic EL element may be covered, and it may be concave plate shape or flat plate shape. Moreover, transparency and electrical insulation are not particularly limited.
具体的には、ガラス板・ガラスフィルム、ポリマー板・ポリマーフィルム、金属板・金属フィルム等が挙げられる。ガラス板・ガラスフィルムとしては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を挙げることができる。また、ポリマー板・ポリマーフィルムとしては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリイミド、ポリエーテルサルファイド、ポリサルフォン等を挙げることができる。金属板・金属フィルムとしては、ステンレス、鉄、銅、アルミニウム、マグネシウム、ニッケル、亜鉛、クロム、チタン、モリブテン、シリコン、ゲルマニウム及びタンタルからなる群から選ばれる一種以上の金属又は合金からなるものが挙げられる。 Specific examples include a glass plate / glass film, a polymer plate / polymer film, and a metal plate / metal film. Examples of the glass plate / glass film include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate / polymer film include polycarbonate, acrylic, polyethylene terephthalate, polyethylene naphthalate, polyimide, polyether sulfide, and polysulfone. Examples of the metal plate / metal film include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum. It is done.
本発明においては、有機EL素子を薄膜化できるということからガラスフィルム、ポリマーフィルム、金属フィルムを好ましく使用することができる。更には、ポリマーフィルムは、酸素透過度10−3g/(m2・24h)以下、水蒸気透過度10−3g/(m2・24h)以下のものであることが好ましい。また、前記の水蒸気透過度、酸素透過度がいずれも10−5g/(m2・24h)以下であることが、更に好ましい。In the present invention, a glass film, a polymer film, and a metal film can be preferably used because the organic EL element can be thinned. Furthermore, the polymer film preferably has an oxygen permeability of 10 −3 g / (m 2 · 24 h) or less and a water vapor permeability of 10 −3 g / (m 2 · 24 h) or less. Moreover, it is more preferable that both the water vapor permeability and the oxygen permeability are 10 −5 g / (m 2 · 24 h) or less.
封止部材を凹状に加工するのは、サンドブラスト加工、化学エッチング加工等が使われる。接着剤として具体的には、アクリル酸系オリゴマー、メタクリル酸系オリゴマーの反応性ビニル基を有する光硬化及び熱硬化型接着剤、2−シアノアクリル酸エステル等の湿気硬化型等の接着剤を挙げることができる。また、エポキシ系等の熱及び化学硬化型(二液混合)を挙げることができる。また、ホットメルト型のポリアミド、ポリエステル、ポリオレフィンを挙げることができる。また、カチオン硬化タイプの紫外線硬化型エポキシ樹脂接着剤を挙げることができる。 For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used. Specific examples of the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to. Moreover, heat | fever and chemical curing types (two-component mixing), such as an epoxy type, can be mentioned. Moreover, hot-melt type polyamide, polyester, and polyolefin can be mentioned. Moreover, a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
前記接着剤中に乾燥剤を分散させておいてもよい。封止部分への接着剤の塗布は、市販のディスペンサーを使ってもよいし、スクリーン印刷のように印刷してもよい。 A desiccant may be dispersed in the adhesive. Application | coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print it like screen printing.
また、有機層を挟み支持基板と対向する側の電極の外側に、該電極と有機層を被覆し、支持基板と接する形で無機物、有機物の層を形成し封止膜とすることも好適にできる。この場合、該膜を形成する材料としては、水分や酸素等素子の劣化をもたらすものの浸入を抑制する機能を有する材料であればよく、例えば、酸化ケイ素、二酸化ケイ素、窒化ケイ素等を用いることができる。更に、該膜の脆弱性を改良するためにこれら無機層と有機材料からなる層の積層構造を持たせることが好ましい。これらの膜の形成方法については、特に限定はなく、例えば真空蒸着法、スパッタリング法、反応性スパッタリング法、分子線エピタキシー法、クラスターイオンビーム法、イオンプレーティング法、プラズマ重合法、大気圧プラズマ重合法、プラズマCVD法、レーザーCVD法、熱CVD法、コーティング法等を用いることができる。 In addition, it is also preferable to coat the electrode and the organic layer on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and form an inorganic or organic layer in contact with the support substrate to form a sealing film. it can. In this case, the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can. Furthermore, in order to improve the brittleness of the film, it is preferable to have a laminated structure of these inorganic layers and layers made of organic materials. The method for forming these films is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
封止部材と有機EL素子の表示領域との間隙には、気相及び液相では、窒素、アルゴン等の不活性気体や、フッ化炭化水素、シリコンオイルのような不活性液体を注入することが好ましい。また、真空とすることも可能である。また、内部に吸湿性化合物を封入することもできる。 In the gap between the sealing member and the display area of the organic EL element, an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil is injected in the gas phase and the liquid phase. Is preferred. A vacuum can also be used. Moreover, a hygroscopic compound can also be enclosed inside.
吸湿性化合物としては、例えば、金属酸化物(例えば、酸化ナトリウム、酸化カリウム、酸化カルシウム、酸化バリウム、酸化マグネシウム、酸化アルミニウム等)、硫酸塩(例えば、硫酸ナトリウム、硫酸カルシウム、硫酸マグネシウム、硫酸コバルト等)、金属ハロゲン化物(例えば、塩化カルシウム、塩化マグネシウム、フッ化セシウム、フッ化タンタル、臭化セリウム、臭化マグネシウム、沃化バリウム、沃化マグネシウム等)、過塩素酸類(例えば過塩素酸バリウム、過塩素酸マグネシウム等)等が挙げられ、硫酸塩、金属ハロゲン化物及び過塩素酸類においては無水塩が好適に用いられる。 Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg, calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide, etc.), perchloric acids (eg, barium perchlorate) , Magnesium perchlorate, etc.), and anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.
《保護膜、保護板》
有機層を挟み支持基板と対向する側の封止膜又は封止用フィルムの外側に、素子の機械的強度を高めるために、保護膜又は保護板を設けてもよい。特に、封止が封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜、保護板を設けることが好ましい。これに使用することができる材料としては、上記封止に用いたのと同様なガラスフィルム、ポリマーフィルム、金属フィルム等を用いることができるが、軽量かつ薄膜化ということからポリマーフィルムを用いることが好ましい。《Protective film, protective plate》
In order to increase the mechanical strength of the element, a protective film or a protective plate may be provided outside the sealing film or sealing film on the side facing the support substrate with the organic layer interposed therebetween. In particular, when sealing is performed with a sealing film, the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate. As a material that can be used for this, the same glass film, polymer film, metal film, and the like as those used for the sealing can be used. However, a polymer film is used because it is lightweight and thin. preferable.
《用途》
上述した実施形態の有機EL素子は、面発光体であるため各種の発光光源として用いることができる。例えば、家庭用照明や車内照明等の照明装置、時計や液晶用のバックライト、看板広告用照明、信号機の光源、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるが、これに限定するものではなく、特にカラーフィルターと組み合わせた液晶表示装置のバックライト、照明用光源としての用途に有効に用いることができる。<Application>
Since the organic EL element of the embodiment described above is a surface light emitter, it can be used as various light emission sources. For example, lighting devices such as home lighting and interior lighting, backlights for watches and liquid crystals, lighting for billboard advertisements, light sources for traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, Examples include, but are not limited to, a light source of an optical sensor, and can be effectively used as a backlight of a liquid crystal display device combined with a color filter and a light source for illumination.
《有機EL素子の製造方法》
図1に示す有機EL素子10を製造する場合を例にとって、本発明の有機EL素子の製造方法の一例を具体的に説明する。
まず、基材11上に、陽極12を形成する。次に、陽極12上に、正孔注入層13及び正孔輸送層14をこの順に形成する。次に、極性フッ化溶媒を含有する発光層形成用塗布液を用いて発光層15を形成する。次に、発光層15上に、一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有する電子輸送層形成用塗布液を用いて電子輸送層16を形成する。次に、電子輸送層16上に、電子注入層17及び陰極18を形成する。
なお、有機EL素子10を構成する発光層及び電子輸送層以外の各層の形成方法としては、上記したとおり、湿式法、蒸着及びスパッタ等いずれの方法であってもよい。また、発光層及び電子輸送層の形成についても、湿式法に限らず、蒸着やスパッタ等の方法を用いてもよい。ただし、有機EL素子10を構成するいずれの層も、コストの観点から、湿式法を用いることが好ましい。<< Method for Manufacturing Organic EL Element >>
Taking as an example the case of manufacturing the
First, the
In addition, as above-mentioned as a formation method of layers other than the light emitting layer and electron carrying layer which comprise the
最後に、陰極18を形成した後の素子を封止する。当該素子の封止に用いられる封止手段としては、公知の部材、方法を使用することができる。
以上のようにして有機EL素子10を製造することができる。Finally, the element after the
The
[極性フッ化溶媒]
本発明の有機EL素子の製造方法において、発光層及び電子輸送層の形成には極性フッ化溶媒が用いられることが好ましい。
ここで、極性フッ化溶媒とは、溶媒分子中にフッ素原子を含み、比誘電率が3以上かつ25℃における水への溶解度が5g/L以上である溶媒をいう。
なお、溶解度とは、25℃1気圧において、溶媒1L当たりに溶解する限界の溶質グラム数を指す。[Polar fluorinated solvent]
In the method for producing an organic EL device of the present invention, a polar fluorinated solvent is preferably used for forming the light emitting layer and the electron transport layer.
Here, the polar fluorinated solvent refers to a solvent containing a fluorine atom in a solvent molecule and having a relative dielectric constant of 3 or more and a solubility in water at 25 ° C. of 5 g / L or more.
The solubility means the limit number of grams of solute dissolved per liter of solvent at 25 ° C. and 1 atm.
極性フッ化溶媒の沸点としては、50〜200℃の範囲内が好ましい。50℃以上とすることで、塗布膜乾燥時の蒸発熱によるムラの発生をより確実に抑制できる。200℃以下とすることで、速やかに溶媒を乾燥させることができ、形成される層内の溶媒含有量が低減するため層内の結晶成長をより確実に抑制できるとともに、溶媒の抜け道が粗とならないため密度が向上し電流効率を上昇させることができる。より好ましくは、70〜150℃の範囲内である。 The boiling point of the polar fluorinated solvent is preferably in the range of 50 to 200 ° C. By setting the temperature to 50 ° C. or higher, the occurrence of unevenness due to the heat of evaporation during drying of the coating film can be more reliably suppressed. By setting the temperature to 200 ° C. or lower, the solvent can be quickly dried, and the solvent content in the formed layer is reduced, so that crystal growth in the layer can be more reliably suppressed, and the solvent escape route is rough. Therefore, the density is improved and the current efficiency can be increased. More preferably, it exists in the range of 70-150 degreeC.
極性フッ化溶媒の水分含有量は、極微量であっても発光のクエンチャーとなるため少ない程よく、100ppm以下が好ましく、20ppm以下であることがより好ましい。
また、極性フッ化溶媒中の水分以外の不純物含有量も同様に、極微量であっても発光のクエンチャーとなったり、気泡や乾燥後の膜質低下要因となったりするため少ない程よく、100ppm以下が好ましく、20ppm以下であることがより好ましい。水分以外の不純物としては、酸素や、窒素、アルゴン及び二酸化炭素等の不活性ガス、調製及び精製時に使用される触媒、吸着材及び器具等から持ち込まれる無機化合物又は金属等が挙げられる。The water content of the polar fluorinated solvent is preferably as low as possible since it becomes a luminescence quencher even if it is a very small amount, and is preferably 100 ppm or less, more preferably 20 ppm or less.
Similarly, the content of impurities other than moisture in the polar fluorinated solvent is also preferably 100 ppm or less because it is a quencher for light emission even if it is a very small amount, and it causes bubbles and film quality deterioration after drying. Is preferable, and it is more preferable that it is 20 ppm or less. Examples of impurities other than moisture include oxygen, inert gases such as nitrogen, argon and carbon dioxide, catalysts used during preparation and purification, inorganic compounds or metals brought in from adsorbents and instruments, and the like.
極性フッ化溶媒としては、例えば、フッ化アルコール、フッ化アクリレート、フッ化メタクリレート、フッ化エステル、フッ化エーテル又はフッ化ヒドロキシアルキルベンゼン、フッ化アミンが好ましく、フッ化アルコール、フッ化エステル又はフッ化エーテルがより好ましく、溶解性と乾燥性の観点からフッ化アルコールが更に好ましい。
また、フッ化アルコールの炭素原子数は、沸点及び材料の可溶性の観点から、炭素原子数3〜5であることが好ましく、極性フッ化溶媒が、炭素原子数3〜5のフッ化アルコールを含有することが好ましい。As the polar fluorinated solvent, for example, fluorinated alcohol, fluorinated acrylate, fluorinated methacrylate, fluorinated ester, fluorinated ether or fluorinated hydroxyalkylbenzene, and fluorinated amine are preferable, and fluorinated alcohol, fluorinated ester or fluorinated Ether is more preferable, and fluorinated alcohol is more preferable from the viewpoints of solubility and drying properties.
The number of carbon atoms of the fluorinated alcohol is preferably 3 to 5 carbon atoms from the viewpoint of boiling point and material solubility, and the polar fluorinated solvent contains a fluorinated alcohol having 3 to 5 carbon atoms. It is preferable to do.
フッ素置換位置としては、例えばアルコールであれば水素の位置が挙げられ、フッ素化率としては、層材料の溶解性を損なわない程度であればよく、下層材料を溶出させない程度にフッ素化されていることが望ましい。 Examples of the fluorine substitution position include the position of hydrogen in the case of alcohol, and the fluorination rate may be any degree that does not impair the solubility of the layer material, and is fluorinated to the extent that the lower layer material is not eluted. It is desirable.
フッ化アルコールとしては、例えば、1H,1H−ペンタフルオロプロパノール、6−(パーフルオロエチル)ヘキサノール、1H,1H−ヘプタフルオロブタノール、2−(パーフルオロブチル)エタノール(FBEO)、3−(パーフルオロブチル)プロパノール、6−(パーフルオロブチル)ヘキサノール、2−パーフルオロプロポキシ−2,3,3,3−テトラフルオロプロパノール、2−(パーフルオロヘキシル)エタノール、3−(パーフルオロヘキシル)プロパノール、6−(パーフルオロヘキシル)ヘキサノール、1H,1H−(パーフルオロヘキシル)ヘキサノール、6−(パーフルオロ−1−メチルエチル)ヘキサノール、1H,1H,3H−テトラフルオロプロパノール(TFPO)、1H,1H,5H−オクタフルオロペンタノール(OFAO)、1H,1H,7H−ドデカフルオロヘプタノール(DFHO)、2H−ヘキサフルオロ−2−プロパノール、1H,1H,3H−ヘキサフルオロブタノール(HFBO)、2,2,3,3,4,4,5,5−オクタフルオロ−1,6−ヘキサンジオール、2,2−ビス(トリフルオロメチル)プロパノール、1H,1H−トリフルオロエタノール(TFEO)等が挙げられるが、前述の沸点及び層材料の溶解性の観点からTFPO、OFAO及びHFBOが好ましい。
また、フッ化エーテルとしては、例えば、ヘキサフルオロジメチルエーテル、ペルフルオロジメトキシメタン、ペルフルオロオキセタン、ペルフルオロ−1,3−ジオキソラン、1,1,2,2−テトラフルオロエチル−2,2,3,3−テトラフルオロプロピルエーテル等が挙げられる。
また、フッ化エステルとしては、例えば、メチルパーフルオロブチレート、エチルパーフルオロブチレート、メチルパーフルオロプロピオネート、メチルジフルオロアセテート、エチルジフルオロアセテート、メチル−2−トリフルオロメチルー3,3,3−トリフルオロプロピオネート等が挙げられる。Examples of the fluorinated alcohol include 1H, 1H-pentafluoropropanol, 6- (perfluoroethyl) hexanol, 1H, 1H-heptafluorobutanol, 2- (perfluorobutyl) ethanol (FBEO), 3- (perfluoro Butyl) propanol, 6- (perfluorobutyl) hexanol, 2-perfluoropropoxy-2,3,3,3-tetrafluoropropanol, 2- (perfluorohexyl) ethanol, 3- (perfluorohexyl) propanol, 6 -(Perfluorohexyl) hexanol, 1H, 1H- (perfluorohexyl) hexanol, 6- (perfluoro-1-methylethyl) hexanol, 1H, 1H, 3H-tetrafluoropropanol (TFPO), 1H, 1H, 5H -Octafull Lopentanol (OFAO), 1H, 1H, 7H-dodecafluoroheptanol (DFHO), 2H-hexafluoro-2-propanol, 1H, 1H, 3H-hexafluorobutanol (HFBO), 2,2,3,3,4 , 4,5,5-octafluoro-1,6-hexanediol, 2,2-bis (trifluoromethyl) propanol, 1H, 1H-trifluoroethanol (TFEO) and the like. From the viewpoint of the solubility of the material, TFPO, OFAO and HFBO are preferable.
Examples of the fluorinated ether include hexafluorodimethyl ether, perfluorodimethoxymethane, perfluorooxetane, perfluoro-1,3-dioxolane, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetra. Examples include fluoropropyl ether.
Examples of the fluorinated ester include methyl perfluorobutyrate, ethyl perfluorobutyrate, methyl perfluoropropionate, methyl difluoroacetate, ethyl difluoroacetate, methyl-2-trifluoromethyl-3,3,3- Examples thereof include trifluoropropionate.
発光層形成用塗布液中、極性フッ化溶媒の含有量は90〜99.95質量%であることが好ましい。
電子輸送層形成用塗布液中、本発明の一般式(1)で表される構造を有する化合物の含有量は0.05〜10質量%、極性フッ化溶媒の含有量は90〜99.95質量%であることが好ましい。
また、極性フッ化溶媒としては、2種以上の極性フッ化溶媒の混合溶媒でもよいし、極性フッ化溶媒と極性フッ化溶媒以外の溶媒との混合溶媒でもよい。例えば、フッ化アルコールとアルコールとの混合溶媒等を用いることができる。混合溶媒を用いる場合、極性フッ化溶媒の含有量は50質量%以上であることが好ましい。In the light emitting layer forming coating solution, the content of the polar fluorinated solvent is preferably 90 to 99.95% by mass.
In the coating liquid for forming an electron transport layer, the content of the compound having a structure represented by the general formula (1) of the present invention is 0.05 to 10% by mass, and the content of the polar fluorinated solvent is 90 to 99.95. It is preferable that it is mass%.
The polar fluorinated solvent may be a mixed solvent of two or more polar fluorinated solvents, or a mixed solvent of a polar fluorinated solvent and a solvent other than the polar fluorinated solvent. For example, a mixed solvent of fluorinated alcohol and alcohol can be used. When using a mixed solvent, the content of the polar fluorinated solvent is preferably 50% by mass or more.
以上説明したように、本発明によれば、高効率、長寿命、かつ屈曲耐性のある有機エレクトロルミネッセンス素子を提供することができる。
また、高生産性のポテンシャルがある塗布型の有機EL素子に適した材料を用いて、湿式法で各構成層を形成することができる。そのため、製造コストが低減され、経済性に優れている。As described above, according to the present invention, an organic electroluminescence element having high efficiency, long life, and bending resistance can be provided.
Further, each constituent layer can be formed by a wet method using a material suitable for a coating type organic EL element having a high productivity potential. Therefore, the manufacturing cost is reduced and the cost is excellent.
以下、実施例を挙げて本発明を具体的に説明するが、本発明はこれらに限定されるものではない。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.
以下の各実施例において用いる溶媒を表9に示す。 Table 9 shows the solvents used in the following examples.
また、以下の各実施例において用いるET−1等は、本明細書中に記載の表1〜8のET−1等に対応する。また、以下の各実施例において用いる、ホスト化合物(H−1等)、発光ドーパント(Dp−1等)、及び、比較例の電子輸送層材料(EA−1等)を以下に示す。なお、表中、イオン化ポテンシャルの値は、小数点第3位を四捨五入した値であり、分子双極子モーメントの値は、小数点第2位を四捨五入した値である。 Moreover, ET-1 etc. which are used in each following Example respond | correspond to ET-1 etc. of Tables 1-8 described in this specification. Moreover, the host compound (H-1 etc.), the light emission dopant (Dp-1 etc.), and the electron transport layer material (EA-1 etc.) of a comparative example used in each of the following examples are shown below. In the table, the ionization potential value is a value obtained by rounding off the third decimal place, and the molecular dipole moment value is obtained by rounding off the second decimal place.
[実施例1]
《有機EL素子101の作製》
以下のように、基材上に、陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極を積層して封止し、ボトムエミッション型の有機EL素子101を作製した。[Example 1]
<< Production of Organic EL Element 101 >>
As shown below, an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode are laminated and sealed on the base material to form a bottom emission type organic EL device 101. Was made.
(基材の準備)
まず、ポリエチレンナフタレートフィルム(帝人デュポン社製、以下、PENと略記する。)の陽極を形成する側の全面に、特開2004−68143号公報に記載の構成の大気圧プラズマ放電処理装置を用いて、SiOxからなる無機物のガスバリアー層を層厚500nmとなるように形成した。これにより、酸素透過度0.001mL/(m2・24h)以下、水蒸気透過度0.001g/(m2・24h)以下のガスバリアー性を有する可撓性の基材を作製した。(Preparation of base material)
First, an atmospheric pressure plasma discharge treatment apparatus having a configuration described in Japanese Patent Application Laid-Open No. 2004-68143 is used on the entire surface of a polyethylene naphthalate film (manufactured by Teijin DuPont, hereinafter abbreviated as PEN) on the side where the anode is formed. Then, an inorganic gas barrier layer made of SiO x was formed to a thickness of 500 nm. Thus, a flexible base material having a gas barrier property with an oxygen permeability of 0.001 mL / (m 2 · 24 h) or less and a water vapor permeability of 0.001 g / (m 2 · 24 h) or less was produced.
(陽極の形成)
上記基材上に厚さ120nmのITO(インジウム・スズ酸化物)をスパッタ法により製膜し、フォトリソグラフィー法によりパターニングを行い、陽極を形成した。なお、パターンは発光領域の面積が5cm×5cmになるようなパターンとした。(Formation of anode)
An ITO (indium tin oxide) film having a thickness of 120 nm was formed on the substrate by sputtering, and patterned by photolithography to form an anode. The pattern was such that the area of the light emitting region was 5 cm × 5 cm.
(正孔注入層の形成)
陽極を形成した基材をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。そして、陽極を形成した基材上に、特許第4509787号公報の実施例16と同様に調製したポリ(3,4−エチレンジオキシチオフェン)/ナフィオン(登録商標))の分散液をイソプロピルアルコールで希釈した2質量%溶液をダイコート法にて塗布、自然乾燥し、層厚40nmの正孔注入層を形成した。(Formation of hole injection layer)
The substrate on which the anode was formed was subjected to ultrasonic cleaning with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes. Then, a dispersion of poly (3,4-ethylenedioxythiophene) / Nafion (registered trademark) prepared in the same manner as in Example 16 of Japanese Patent No. 4509787 was used with isopropyl alcohol on the base material on which the anode was formed. A diluted 2% by mass solution was applied by a die coating method and naturally dried to form a hole injection layer having a layer thickness of 40 nm.
(正孔輸送層の形成)
次に、正孔注入層を形成した基材を、窒素ガス(グレードG1)を用いた窒素雰囲気下に移し、下記組成の正孔輸送層形成用塗布液を用いて、ダイコート法にて5m/minで塗布、自然乾燥した後に、130℃で30分間保持し、層厚30nmの正孔輸送層を形成した。(Formation of hole transport layer)
Next, the base material on which the hole injection layer was formed was transferred to a nitrogen atmosphere using nitrogen gas (grade G1), and a coating liquid for forming a hole transport layer having the following composition was used to form a 5 m / After being applied for min and dried naturally, it was held at 130 ° C. for 30 minutes to form a hole transport layer having a layer thickness of 30 nm.
〈正孔輸送層形成用塗布液〉
正孔輸送材料(下記化合物(60))(質量平均分子量Mw=80000)
10質量部
クロロベンゼン 3000質量部<Coating liquid for hole transport layer formation>
Hole transport material (the following compound (60)) (mass average molecular weight Mw = 80000)
10 parts by mass Chlorobenzene 3000 parts by mass
(発光層の形成)
次に、正孔輸送層を形成した基材を、下記組成の発光層形成用塗布液を用い、ダイコート法にて5m/minで塗布し、自然乾燥した後に、120℃で30分間保持し、層厚50nmの発光層を形成した。(Formation of light emitting layer)
Next, the base material on which the hole transport layer was formed was applied at 5 m / min by a die coating method using a light emitting layer forming coating solution having the following composition, naturally dried, and then held at 120 ° C. for 30 minutes. A light emitting layer having a layer thickness of 50 nm was formed.
〈発光層形成用塗布液〉
ホスト化合物H−1(Ip:−5.39eV) 9質量部
リン光発光ドーパントDp−2(Ip:−4.40eV)1質量部
酢酸イソプロピル 2000質量部
ここで、発光ドーパントとホスト化合物のIpの差( ΔIp)は−0.99eVである。<Light emitting layer forming coating solution>
Host compound H-1 (Ip: -5.39 eV) 9 parts by mass Phosphorescent dopant Dp-2 (Ip: -4.40 eV) 1 part by mass Isopropyl acetate 2000 parts by mass Here, the emission dopant and host compound Ip The difference (ΔIp) is −0.99 eV.
(電子輸送層の形成)
次に、発光層を形成した基材を、下記組成の電子輸送層形成用塗布液を用い、ダイコート法にて5m/minで塗布し、自然乾燥した後に、80℃で30分間保持し、層厚30nmの電子輸送層を形成した。(Formation of electron transport layer)
Next, the base material on which the light emitting layer was formed was applied at 5 m / min by a die coating method using an electron transport layer forming coating solution having the following composition, naturally dried, and then kept at 80 ° C. for 30 minutes, An electron transport layer having a thickness of 30 nm was formed.
〈電子輸送層形成用塗布液〉
ET−2 6質量部
1H,1H,3H−テトラフルオロプロパノール(TFPO) 2000質量部<Coating liquid for electron transport layer formation>
ET-2 6 parts by mass 1H, 1H, 3H-tetrafluoropropanol (TFPO) 2000 parts by mass
(電子注入層、陰極の形成)
続いて、基板を大気に曝露することなく真空蒸着装置へ取り付けた。また、モリブデン製抵抗加熱ボートにフッ化ナトリウム及びフッ化カリウムを入れたものを真空蒸着装置に取り付け、真空槽を4×10−5Paまで減圧した。その後、ボートに通電して加熱し、フッ化ナトリウムを0.02nm/秒で前記電子輸送層上に蒸着し、膜厚1nmの薄膜を形成した。同様に、フッ化カリウムを0.02nm/秒でフッ化ナトリウム薄膜上に蒸着し、層厚1.5nmの電子注入層を形成した。
引き続き、アルミニウムを蒸着して厚さ100nmの陰極を形成した。(Formation of electron injection layer and cathode)
Subsequently, the substrate was attached to a vacuum deposition apparatus without being exposed to the atmosphere. Moreover, what put sodium fluoride and potassium fluoride in the resistance heating boat made from molybdenum was attached to the vacuum evaporation system, and the vacuum tank was pressure-reduced to 4 * 10 < -5 > Pa. Thereafter, the boat was energized and heated, and sodium fluoride was deposited on the electron transport layer at 0.02 nm / second to form a thin film having a thickness of 1 nm. Similarly, potassium fluoride was vapor-deposited on the sodium fluoride thin film at 0.02 nm / second to form an electron injection layer having a layer thickness of 1.5 nm.
Subsequently, aluminum was deposited to form a cathode having a thickness of 100 nm.
(封止)
以上の工程により形成した積層体に対し、市販のロールラミネート装置を用いて封止基材を接着した。
封止基材として、可撓性を有する厚さ30μmのアルミニウム箔(東洋アルミニウム(株)製)に、ドライラミネーション用の2液反応型のウレタン系接着剤を用いて層厚1.5μmの接着剤層を設け、厚さ12μmのポリエチレンテレフタレート(PET)フィルムをラミネートしたものを作製した。(Sealing)
The sealing base material was adhere | attached on the laminated body formed by the above process using the commercially available roll laminating apparatus.
Adhesion as a sealing substrate with a thickness of 1.5 μm using a flexible aluminum foil (manufactured by Toyo Aluminum Co., Ltd.) with a thickness of 30 μm using a two-component reaction type urethane adhesive for dry lamination. An agent layer was provided, and a laminate of a polyethylene terephthalate (PET) film having a thickness of 12 μm was prepared.
封止用接着剤として熱硬化性接着剤を、ディスペンサーを使用して封止基材のアルミニウム箔の接着面(つや面)に沿って厚さ20μmで均一に塗布した。これを100Pa以下の真空下で12時間乾燥させた。更に、その封止基材を露点温度−80℃以下、酸素濃度0.8ppmの窒素雰囲気下へ移動して、12時間以上乾燥させ、封止用接着剤の含水率が100ppm以下となるように調整した。 A thermosetting adhesive as a sealing adhesive was uniformly applied at a thickness of 20 μm along the adhesive surface (shiny surface) of the aluminum foil of the sealing substrate using a dispenser. This was dried under a vacuum of 100 Pa or less for 12 hours. Furthermore, the sealing substrate is moved to a nitrogen atmosphere having a dew point temperature of −80 ° C. or lower and an oxygen concentration of 0.8 ppm, and is dried for 12 hours or more so that the moisture content of the sealing adhesive is 100 ppm or lower. It was adjusted.
熱硬化性接着剤としては下記の(A)〜(C)を混合したエポキシ系接着剤を用いた。
(A)ビスフェノールAジグリシジルエーテル(DGEBA)
(B)ジシアンジアミド(DICY)
(C)エポキシアダクト系硬化促進剤As the thermosetting adhesive, an epoxy adhesive mixed with the following (A) to (C) was used.
(A) Bisphenol A diglycidyl ether (DGEBA)
(B) Dicyandiamide (DICY)
(C) Epoxy adduct curing accelerator
上記封止基材を上記積層体に対して密着・配置して、圧着ロールを用いて、圧着ロール温度100℃、圧力0.5MPa、装置速度0.3m/minの圧着条件で密着封止した。
以上のようにして、上述の図1に示す構成の有機EL素子と同様の形態の有機EL素子101を作製した。The sealing base material was closely attached to the laminate, and was tightly sealed with a pressure roll under pressure conditions of a pressure roll temperature of 100 ° C., a pressure of 0.5 MPa, and an apparatus speed of 0.3 m / min. .
As described above, an organic EL element 101 having the same form as the organic EL element having the configuration shown in FIG. 1 was manufactured.
《有機EL素子102〜144の作製》
上記有機EL素子101の作製において、電子輸送層の形成について表10に記載の条件に変更した以外は、同様な方法で有機EL素子102〜144を作製した。<< Production of Organic EL Elements 102 to 144 >>
In the production of the organic EL element 101, organic EL elements 102 to 144 were produced in the same manner except that the formation of the electron transport layer was changed to the conditions shown in Table 10.
[評価方法]
(1)発光効率の測定
発光効率の測定は、室温(25℃)で、2.5mA/cm2の定電流密度条件下による点灯を行い、分光放射輝度計CS−2000(コニカミノルタ社製)を用いて、各素子の発光輝度を測定し、当該電流値における発光効率(外部取り出し効率)を求めた。そして、有機EL素子137(比較)の発光効率を100とする相対値として、各素子の発光効率を求めた。[Evaluation methods]
(1) Measurement of luminous efficiency Luminous efficiency is measured at room temperature (25 ° C) at a constant current density of 2.5 mA / cm 2 and a spectral radiance meter CS-2000 (manufactured by Konica Minolta). Was used to measure the light emission luminance of each element, and the light emission efficiency (external extraction efficiency) at the current value was determined. And the luminous efficiency of each element was calculated | required as the relative value which sets the luminous efficiency of the organic EL element 137 (comparison) to 100.
(2)発光寿命の測定
発光寿命の測定は、有機EL素子を室温25℃、湿度55%RHの条件下で連続駆動させ、上記分光放射輝度計CS−2000を用いて輝度を測定し、測定した輝度が半減する時間(半減寿命)を寿命の尺度として求めた。駆動条件は、連続駆動開始時に10000cd/m2となる電流値とした。そして、有機EL素子137(比較)の発光寿命を100とする相対値として、各素子の発光寿命を求めた。(2) Measurement of luminescence lifetime The luminescence lifetime is measured by continuously driving an organic EL element under conditions of room temperature 25 ° C. and humidity 55% RH, and measuring the luminance using the spectral radiance meter CS-2000. The time (half life) during which the brightness was reduced by half was determined as a measure of life. The driving condition was set to a current value of 10,000 cd / m 2 at the start of continuous driving. And the light emission lifetime of each element was calculated | required as the relative value which sets the light emission lifetime of the organic EL element 137 (comparison) to 100.
(3)高温保存後の安定性の評価
各有機EL素子を、85℃で24時間保存した後、保存前後における2.5mA/cm2の定電流駆動における各素子の発光輝度を測定し、各輝度比を下式に従って求め、これを保存性の尺度とした。
保存性(%)=保存後の輝度(2.5mA/cm2)/保存前の輝度(2.5mA/cm2)×100(3) Evaluation of stability after storage at high temperature After each organic EL device was stored at 85 ° C. for 24 hours, the light emission luminance of each device in a constant current drive of 2.5 mA / cm 2 before and after storage was measured. The luminance ratio was determined according to the following formula, and this was used as a measure of storage stability.
Storage stability (%) = luminance after storage ( 2.5 mA / cm 2 ) / luminance before storage ( 2.5 mA / cm 2 ) × 100
(4)屈曲耐性試験後の安定性の評価
各有機EL素子を、Al蒸着PET封止面を上にして、15mmφのローラーに巻回させ、続けてそれを全て平らに戻す、といった屈曲試験を100回繰り返し実施した。屈曲試験の実施後、2.5mA/cm2の定電流駆動における各素子の駆動電圧を測定、各駆動電圧比を下式に従って求め、これを屈曲耐性の尺度とした。
屈曲耐性(%)=屈曲耐性試験後の電圧(2.5mA/cm2)/試験前の電圧(2.5mA/cm2)×100(4) Stability evaluation after bending resistance test Each organic EL element is wound on a 15 mmφ roller with the Al-deposited PET sealing surface facing up, and then it is continuously bent back. Repeated 100 times. After the bending test, the driving voltage of each element in the constant current driving of 2.5 mA / cm 2 was measured, and each driving voltage ratio was determined according to the following equation, and this was used as a measure of bending resistance.
Flex resistance (%) = voltage after flex resistance test ( 2.5 mA / cm 2 ) / voltage before test ( 2.5 mA / cm 2 ) × 100
(5)極性フッ化溶媒含有量の測定
30mm角のガラス基板上に上記有機EL素子と同様に各層を形成した後に、トルエンを浸したクリーンワイパーで薄膜積層体を一部剥ぎ取り、サンユー電子社製SC−701 MkII ECOでAg薄膜をスパッタ後、Veeco社製WYKOを用いて薄膜積層体をはぎ取った境目の段差を計測し膜厚を決定した。更に、30mm角のガラス基板上に上記と同様に各薄膜積層体を形成後、10mm角程度にウェハーを切削し、前後の質量比から膜面積を求めた。上記面積が決定されたシリコンウェハーを電子科学社製の昇温熱脱離分析装置により測定し、使用したフッ化溶媒に対応するマスフラグメントスペクトルから、脱離ガス成分を定量し各有機層積層体の体積あたりのフッ化溶媒の質量比を求めた。なお、表中、各フッ化溶媒に対応するマスフラグメントスペクトルに優位なピークが検出されなかった場合を、「n.d.」(not detected)と示す。
これらの結果を表10に示す。(5) Measurement of polar fluorinated solvent content After each layer was formed on a 30 mm square glass substrate in the same manner as the above organic EL device, a part of the thin film laminate was peeled off with a clean wiper soaked in toluene. After sputtering the Ag thin film with SC-701 MkII ECO manufactured by SC-701, the step difference at the boundary where the thin film stack was peeled off was measured using WYKO manufactured by Veeco to determine the film thickness. Further, after each thin film laminate was formed on a 30 mm square glass substrate in the same manner as described above, the wafer was cut to about 10 mm square, and the film area was determined from the mass ratio before and after. The silicon wafer with the determined area was measured with a thermal desorption analyzer manufactured by Denshi Kagaku Co., Ltd., and the desorbed gas components were quantified from the mass fragment spectrum corresponding to the fluorinated solvent used. The mass ratio of the fluorinated solvent per volume was determined. In the table, the case where no dominant peak is detected in the mass fragment spectrum corresponding to each fluorinated solvent is indicated as “nd” (not detected).
These results are shown in Table 10.
表10から、本発明の有機EL素子101〜136は、比較例の有機EL素子137〜144に対して、発光効率に優れ、発光寿命が長く、高温保存後の安定性及び屈曲耐性に優れていることがわかる。 From Table 10, the organic EL elements 101 to 136 of the present invention are superior in luminous efficiency, have a long emission lifetime, and have excellent stability and bending resistance after high-temperature storage compared to the organic EL elements 137 to 144 of the comparative example. I understand that.
[実施例2]
《有機EL素子201〜206の作製》
上記有機EL素子101の作製において、発光層及び電子輸送層の形成について表11に記載の条件に変更した以外は、同様な方法で有機EL素子201〜206を作製した。
そして、実施例1と同様の評価を行った。なお、発光効率及び発光寿命は、有機EL素子204(比較)の発光効率及び発光寿命を100とする相対値として、各素子の発光効率及び発光寿命を求めた。これらの結果を表11に示す。[Example 2]
<< Production of Organic EL Elements 201-206 >>
In the production of the organic EL element 101, organic EL elements 201 to 206 were produced in the same manner except that the formation of the light emitting layer and the electron transport layer was changed to the conditions described in Table 11.
And evaluation similar to Example 1 was performed. The light emission efficiency and the light emission lifetime were obtained as relative values with the light emission efficiency and the light emission lifetime of the organic EL element 204 (comparative) as 100. These results are shown in Table 11.
表11から、本発明の有機EL素子201〜203は、比較例の有機EL素子204〜206に対して、発光効率に優れ、発光寿命が長く、高温保存後の安定性及び屈曲耐性に優れていることがわかる。 From Table 11, the organic EL elements 201 to 203 of the present invention are superior in luminous efficiency, have a long emission lifetime, and have excellent stability and bending resistance after high temperature storage, compared to the organic EL elements 204 to 206 of the comparative example. I understand that.
以上のとおり、本発明によれば、高効率、長寿命、かつ屈曲耐性のある有機EL素子を提供するという課題を解決することができる。更に、本発明の有機EL素子は、高温保存時の輝度低下が抑制される。 As described above, according to the present invention, it is possible to solve the problem of providing an organic EL element having high efficiency, long life, and bending resistance. Furthermore, in the organic EL device of the present invention, a decrease in luminance during high temperature storage is suppressed.
10 有機エレクトロルミネッセンス素子
11 基材
12 陽極
13 正孔注入層
14 正孔輸送層
15 発光層
16 電子輸送層
17 電子注入層
18 陰極10 Organic electroluminescence device
DESCRIPTION OF
Claims (13)
前記発光層のホスト化合物のイオン化ポテンシャルが前記発光層の発光ドーパントのイオン化ポテンシャルより0.3eV以上深く、
前記電子輸送層に含まれる少なくとも1つの有機化合物の分子双極子モーメントが6.0デバイ以上である有機エレクトロルミネッセンス素子。An organic electroluminescence device comprising a light emitting layer and an electron transport layer adjacent to the light emitting layer between an anode and a cathode,
The ionization potential of the host compound of the light emitting layer is 0.3 eV or more deeper than the ionization potential of the light emitting dopant of the light emitting layer;
The organic electroluminescent element whose molecular dipole moment of the at least 1 organic compound contained in the said electron carrying layer is 6.0 debyes or more.
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CN109983597B (en) | 2021-09-07 |
US11444251B2 (en) | 2022-09-13 |
CN109983597A (en) | 2019-07-05 |
WO2018100907A1 (en) | 2018-06-07 |
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